1. A process for preparing a protected trifluorothreonine having the structure:
or a salt thereof or a carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
the process comprising the steps of
a) providing an alkene compound having the structure:
wherein P1 is a hydroxyl protecting group;
b) dihydroxylation of the alkene compound to yield a dihydroxyl compound having the structure:
c) conversion of the dihydroxyl compound to a monohydroxyl compound having the structure:
d) protection of the monohydroxyl compound to yield an azide compound having the structure:
e) transformation of the azide compound to yield an amino compound having the structure:
f) protection of the amino compound to yield a protected amine compound having the structure:
and
g) oxidation of the protected amine compound to yield the protected trifluorothreonine or the salt thereof or the carboxylate derivative thereof.
2-5. (canceled)
6. The process of claim 1, wherein the providing step comprises the steps of:
a) reducing a ketone having the structure:
wherein R is an alkyl group,
to yield an alcohol having the structure:
b) eliminating the hydroxyl group of the alcohol to yield an acrylate having the structure:
and
c) reducing the acrylate and protecting the product to yield an alkene compound having the structure:
7. The process of claim 1, wherein the dihydroxylation step is asymmetric dihydroxylation.
8-9. (canceled)
10. The process of claim 1, wherein the dihydroxyl compound has the structure:
11. The process of claim 1, wherein the conversion step comprises the steps of:
a) reacting the dihydroxyl compound with a thionyl halide, followed by treatment with NaIO4 and RuCl3; and
b) reacting the product of step (a) with NaN3.
12. The process of claim 1, wherein the monohydroxyl compound has the structure:
13. The process of claim 1, wherein the protection of the monohydroxyl compound step comprises treatment with isobutene.
14. The process of claim 1, wherein the azide compound has the structure:
15. The process of claim 1, wherein the transformation step comprises the steps of:
a) treatment with DIBAL-H; and
b) catalytic hydrogenation.
16. The process of claim 1, wherein the amino compound has the structure:
17. (canceled)
18. The process of claim 1, wherein the protected amine compound has the structure:
19. The process of claim 1, wherein the protected trifluorothreonine has the structure:
20. (canceled)
21. A compound having the structure:
or a salt thereof or carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group.
22-24. (canceled)
25. The compound of claim 21, having the structure:
26. The compound of claim 21, having the structure:
27. (2R,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-4,4,4-trifluorobutanoic acid.
28. (2S,3R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-4,4,4-trifluorobutanoic acid
29. (canceled)
30. A peptide comprising at least one residue of the product of a process for preparing a protected trifluorothreonine having the structure:
or a salt thereof or a carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
the process comprising the steps of:
a) providing an alkene compound having the structure:
wherein P1 is a hydroxyl protecting group;
b) dihydroxylation of the alkene compound to yield a dihydroxyl compound having the structure:
c) conversion of the dihydroxyl compound to a monohydroxyl compound having the structure:
d) protection of the monohydroxyl compound to yield an azide compound having the structure:
e) transformation of the azide compound to yield an amino compound having the structure:
f) protection of the amino compound to yield a protected amine compound having the structure:
and
g) oxidation of the protected amine compound to yield the protected trifluorothreonine or the salt thereof or the carboxylate derivative thereof, or
at least one residue of a compound having the structure:
or a salt thereof or carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group.
31. The peptide of claim 30, having the structure:
Z-D-Phe-Cys-M-D-Trp-Lys-A-Cys-A-X,
wherein each A independently comprises a residue of threonine or
a residue of a process for preparing a protected trifluorothreonine having the structure:
or a salt thereof or a carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
the process comprising the steps of:
a) providing an alkene compound having the structure:
wherein P1 is a hydroxyl protecting group;
b) dihydroxylation of the alkene compound to yield a dihydroxyl compound having the structure:
c) conversion of the dihydroxyl compound to a monohydroxyl compound having the structure:
d) protection of the monohydroxyl compound to yield an azide compound having the structure:
e) transformation of the azide compound to yield an amino compound having the structure:
f) protection of the amino compound to yield a protected amine compound having the structure:
and
g) oxidation of the protected amine compound to yield the protected trifluorothreonine or the salt thereof or the carboxylate derivative thereof, or
a residue of a compound having the structure:
a compound having the structure:
or a salt thereof or carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
wherein M comprises Phe or Tyr or a derivative thereof;
wherein X comprises a terminal end group selected from carboxyl, ester, amide, and alcohol;
wherein Z comprises a terminal end group selected from amino, formyl, acetyl, and succinyl.
32. The peptide of claim 31, having the structure:
Z-D-Phe-Cys-M-D-Trp-Lys-A-Cys-Thr-X,
wherein A is a residue of the product of a process for preparing a protected trifluorothreonine having the structure:
or a salt thereof or a carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
the process comprising the steps of:
a) providing an alkene compound having the structure:
wherein P1 is a hydroxyl protecting group;
b) dihydroxylation of the alkene compound to yield a dihydroxyl compound having the structure:
c) conversion of the dihydroxyl compound to a monohydroxyl compound having the structure:
d) protection of the monohydroxyl compound to yield an azide compound having the structure:
e) transformation of the azide compound to yield an amino compound having the structure:
f) protection of the amino compound to yield a protected amine compound having the structure:
and
g) oxidation of the protected amine compound to yield the protected trifluorothreonine or the salt thereof or the carboxylate derivative thereof, or
a residue of a compound having the structure:
or a salt thereof or carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group.
33. The peptide of claim 31, having the structure:
Z-D-Phe-Cys-M-D-Trp-Lys-Thr-Cys-A-X,
wherein A is a residue of the product of a process for preparing a protected trifluorothreonine having the structure:
or a salt thereof or a carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
the process comprising the steps of:
a) providing an alkene compound having the structure:
wherein P1 is a hydroxyl protecting group;
b) dihydroxylation of the alkene compound to yield a dihydroxyl compound having the structure:
c) conversion of the dihydroxyl compound to a monohydroxyl compound having the structure:
d) protection of the monohydroxyl compound to yield an azide compound having the structure:
e) transformation of the azide compound to yield an amino compound having the structure:
f) protection of the amino compound to yield a protected amine compound having the structure:
and
g) oxidation of the protected amine compound to yield the protected trifluorothreonine or the salt thereof or the carboxylate derivative thereof, or
a residue of a compound having the structure:
or a salt thereof or carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group.
34. The peptide of claim 31, having the structure:
Z-D-Phe-Cys-M-D-Trp-Lys-A-Cys-A-X,
wherein each A independently comprises a residue of the product of a process for preparing a protected trifluorothreonine having the structure:
or a salt thereof or a carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group;
the process comprising the steps of:
a) providing an alkene compound having the structure:
wherein P1 is a hydroxyl protecting group;
b) dihydroxylation of the alkene compound to yield a dihydroxyl compound having the structure:
c) conversion of the dihydroxyl compound to a monohydroxyl compound having the structure:
d) protection of the monohydroxyl compound to yield an azide compound having the structure:
e) transformation of the azide compound to yield an amino compound having the structure:
f) protection of the amino compound to yield a protected amine compound having the structure:
and
g) oxidation of the protected amine compound to yield the protected trifluorothreonine or the salt thereof or the carboxylate derivative thereof, or
a residue of a compound having the structure:
or a salt thereof or carboxylate derivative thereof,
wherein P2 is a hydroxyl protecting group, and
wherein P3 is an amine protecting group.
35-38. (canceled)
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A robotic arm for holding a molding item, the robotic arm comprising:
a mount;
a lifting mechanism mounted to the mount;
a horizontal driving device;
a rotating assembly mounted between the lifting mechanism and the horizontal driving device to rotate the horizontal driving device relative to the lifting mechanism;
a holder mounted on the horizontal driving device for holding the molding item;
wherein the lifting mechanism causes the holder to move relative to the mount in a first direction, the horizontal driving device moves the holder relative to the mount and the lifting mechanism in a second direction perpendicular to the first direction.
2. The robotic arm of claim 1, wherein the lifting mechanism includes a first cylinder assembly mounted to the mount and a first mounting board movably mounted on the first cylinder assembly, the first mounting board retains the rotating assembly to the lifting mechanism.
3. The robotic arm of claim 2, wherein when the first mounting board moves relative to the first cylinder assembly, the first mounting board drives the rotating assembly to move relative to the mount and the lifting mechanism in the first direction.
4. The robotic arm of claim 3, wherein the rotating assembly includes a retaining element and a rotating element rotatably engaging the retaining element.
5. The robotic arm of claim 4, wherein the retaining element is positioned on the first mounting board and the rotating element is positioned on the horizontal driving device.
6. The robotic arm of claim 5, wherein a shaft is affixed to the rotating element and rotatably engages with the retaining element so the rotating element can rotate around the shaft relative to the retaining element.
7. The robotic arm of claim 6, wherein a shaft hole is defined in the retaining element, the shaft is rotatably located in the shaft hole.
8. The robotic arm of claim 7, wherein a distal end of the shaft is wider than the shaft hole preventing the shaft from passing through the shaft hole thereby retaining the rotating element to the retaining element.
9. The robotic arm of claim 8, further including a biasing member coupled between the retaining element and the rotating element.
10. The robotic arm of claim 9, wherein the biasing member exerts a force on the rotating element causing the rotating element to rotate about the shaft relative to the retaining element.
11. The robotic arm of claim 1, wherein the horizontal driving device includes a second cylinder assembly mounted to the rotating assembly and a second mounting board movably mounted in the second cylinder assembly; the holder mounted to the second mounting board.
12. The robotic arm of claim 11, wherein a connecting board connects the holder to the horizontal driving device.
13. The robotic arm of claim 12, wherein one end of the connecting board is retained to the second mounting board and another end of the connecting board is retained to the holder.
14. The robotic arm of claim 13, wherein when the second mounting board moves relative to the second cylinder assembly, the second mounting board drives the connecting board to move relative to the mount and the horizontal driving device in the second direction.
15. The robotic arm of claim 1, wherein the holder includes a holder controlling cylinder mounted to the horizontal driving device and two opposite main jaws located at one end of the holder controlling cylinder; the main jaws is capable of closing to or separating from each other by the holder controlling cylinder, to hold or release the molding item.
16. The robotic arm of claim 15, wherein each main jaw defines a V-shaped clasping groove facing the other main jaw, for firmly holding the molding item on the holder.
17. The robotic arm of claim 16, wherein the holder further includes two opposite main jaws, each secondary jaw positioned on one of the main jaws; the secondary jaws can close to or separate from each other by the holder controlling cylinder, to assist the main jaws to hold the molding item.
18. The robotic arm of claim 17, wherein the distance between the secondary jaws is smaller than the distance between the main jaws so the secondary jaws hold the molding item before the main jaws hold the molding item.
19. The robotic arm of claim 17, wherein each secondary jaw defines a holding groove aligned with corresponding clasping groove, for firmly holding the molding item on the holder.
20. A robotic arm for holding a molding item, the robotic arm comprising:
a mount;
a holder for holding the molding item; and
a rotating assembly mounted between the mount and the holder to rotate the holder relative to the mount.