Claims
- 1. A method of preparing (2R,3S)-3-benzoyl-2-hydroxy-3-phenylpropionate of 4,10β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-1,13α-dihydroxy-7β-methylthiomethyloxy-9-oxo-tax-11-ene, formula (XXXIV),
- 2. The method according to claim 1, wherein said acetylated baccatin is reacted in a Pummerer reaction to obtain said methylthiomethyloxy acetylated baccatin.
- 3. The method according to claim 1, wherein said acetylated baccatin is reacted with dimethyl sulfide and benzoyl peroxide to obtain said methylthiomethyloxy acetylated baccatin.
- 4. The method according to any one of claims 1 to 3, wherein the alkali metal or alkaline earth metal base is at least one compound selected from sodium hexamethyl-disilazide (NaHMDS), potassium hexamethyldisilazide (KHMDS), lithium hexamethyldisilazide (LiHMDS), potassium diisopropylamide (KDA), lithium diisopropylamide (LDA), sodium hydride (NaH), potassium hydride (KH), lithium hydride (LiH), calcium hydride (CaH2), magnesium hydride (MgH2), and n-butylLi.
- 5. The method according to claim 4, wherein said at least one compound is a hexamethyl disilazide.
- 6. The method according to claim 5, wherein said hexamethyl disilazide is sodium hexamethyl disilazide, and R is Na.
- 7. The method according to claim 6, wherein G1 is selected from methoxymethyl (MOM), β-methoxyethoxymethyl (MEM), trialkylsilyl, triphenylmethyl (trityl), TIPSO, tert-butoxycarbonyl (t-BOC), ethoxyethyl (EE), f-MOC, and TROC.
- 8. The method according to claim 7, wherein G1 is ethoxyethyl.
- 9. A method of preparing (2R,3S)-3-benzoyl-2-hydroxy-3-phenylpropionate of 4,10β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-1,13α-dihydroxy-7β-methylthiomethyloxy-9-oxo-tax-11-ene, formula (XXXIV)
- 10. The method according to claim 9, wherein said protected taxoid is reacted in a Pummerer reaction to obtain said methylthiomethyloxy-10-acetyl taxoid.
- 11. The method according to claim 9, wherein said protected taxoid is reacted with dimethyl sulfide and benzoyl peroxide to obtain said methylthiomethyloxy-10-acetyl taxoid.
- 12. The method according to any one of claims 9 to 11, wherein the alkali metal or alkaline earth metal base is at least one compound selected from sodium hexamethyl-disilazide (NaHMDS), potassium hexamethyldisilazide (KHMDS), lithium hexamethyldisilazide (LiHMDS), potassium diisopropylamide (KDA), lithium diisopropylamide (LDA), sodium hydride (NaH), potassium hydride (KH), lithium hydride (LiH), calcium hydride (CaH2), magnesium hydride (MgH2), and n-butylLi.
- 13. The method according to claim 12, wherein said at least one compound is a hexamethyl disilazide.
- 14. The method according to claim 13, wherein said hexamethyl disilazide is sodium hexamethyl disilazide, and R is Na.
- 15. The method according to claim 14, wherein G1 is selected from methoxymethyl (MOM), β-methoxyethoxymethyl (MEM), trialkylsilyl, triphenylmethyl (trityl), TIPSO, tert-butoxycarbonyl (t-BOC), ethoxyethyl (EE), f-MOC, and TROC.
- 16. The method according to claim 15, wherein G1 is ethoxyethyl.
Parent Case Info
[0001] This is a continuation-in-part of U.S. patent application Ser. No. 09/528,448, filed Mar. 17, 2000; which is a continuation-in-part of U.S. patent application Ser. No. 09/271,300, filed Mar. 17, 1999, now U.S. Pat. No. 6,040,466; which is a continuation-in-part of U.S. patent application Ser. No. 08/913,972, filed Sep. 26, 1997, now U.S. Pat. No. 5,889,043; and a continuation of PCT/FR96/00441, filed Mar. 25, 1996. This application is also a continuation-in-part of U.S. patent application Ser. No. 09/516,019, filed Feb. 29, 2000, now U.S. Pat. No.; which is a divisional of 08/481,205, filed Jun. 7, 1995, now U.S. Pat. No. 6,187,916; which is a continuation of 08/383,610, filed Feb. 2, 1995, now abandoned; which is a continuation of 08/011,922, filed Feb. 1, 1993, now abandoned. All of these patents and applications are hereby specifically incorporated herein by reference in their entirety.
Divisions (1)
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Number |
Date |
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Parent |
08481205 |
Jun 1995 |
US |
Child |
09516019 |
Feb 2000 |
US |
Continuations (2)
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Parent |
08383610 |
Feb 1995 |
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Child |
08481205 |
Jun 1995 |
US |
Parent |
08011922 |
Feb 1993 |
US |
Child |
08383610 |
Feb 1995 |
US |
Continuation in Parts (4)
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Number |
Date |
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Parent |
09528448 |
Mar 2000 |
US |
Child |
09797845 |
Mar 2001 |
US |
Parent |
09271300 |
Mar 1999 |
US |
Child |
09528448 |
Mar 2000 |
US |
Parent |
08913972 |
Sep 1997 |
US |
Child |
09271300 |
Mar 1999 |
US |
Parent |
PCT/FR96/00441 |
Mar 1996 |
US |
Child |
09271300 |
Mar 1999 |
US |