(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

Base Information

• Chemical Name: (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate
• CAS No.: 155588-13-9
• Molecular Formula: C₃₇H₅₂O₁₀Si
• Molecular Weight: 684.899

Synonyms:(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

Chemical Property of (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

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Technology Process of (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

There total 115 articles about (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

triethylsilyl chloride (994-30-9) + 13-deoxybaccatin III (155588-14-0) → (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate (155588-13-9)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 17h;

DOI:10.1021/jo011183q

Reference yield: 59.0%

C41H54N2O11SSi (155588-18-4) → C37H52O10Si + (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate (155588-13-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 2h;

DOI:10.1021/ja00107a006

Reference yield:

(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9) → (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate (155588-13-9)

Guidance literature:

Multi-step reaction with 39 steps

1: 1.) Ac₂O, DMAP, Py, 2.) naphthalenesulfonic acid, 3.) NaOMe

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 1.) BH₃*THF, 2.) aq. H₂O₂, aq. NaOH, 3.) pyridinium dichromate

4: 1.) KHMDS / 1.) THF, -78 deg C, 2.) THF

5: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

6: 99 percent / DIBAL / hexane / -78 °C

7: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

8: Py / CH₂Cl₂ / 3 h / Ambient temperature

9: CH₂Cl₂ / 1.5 h / Ambient temperature

10: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

11: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

12: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

13: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

14: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

15: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

16: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

17: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

18: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

19: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

20: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

21: 1.) tBuLi, 3.) tetrabutylammonium fluoride

22: 80 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 11 h / Ambient temperature

23: 65 percent / H₂ / Pd/C / ethanol / 1.25 h / -5 °C

24: 81 percent / NaH / dimethylformamide

25: 93 percent / L-selectride / tetrahydrofuran / 1.25 h / -78 °C

26: 98 percent / KHMDS / tetrahydrofuran / 0.17 h / -78 °C

27: 96 percent / aq. pyridinium p-toluenesulfonate / acetone / 9 h / 75 °C

28: 77 percent / tetrahydrofuran / 0.42 h / -78 - 0 °C

29: 46 percent / Pd(Ph₃P)4, K₂CO₃, molecular sieves 4A / acetonitrile / 16.5 h / 90 °C

30: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

31: 92 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

32: 45 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 10.25 h / Ambient temperature

33: 82 percent / H₂, Pd(OAc)2 / ethanol / 10 h

34: 66 percent / Py, DMAP / 16 h / Ambient temperature

35: 93 percent / tetrahydrofuran; diethyl ether / 0.03 h / -78 °C

36: 1.) OsO₄, Py, 2.) Pb(OAc)4 / 1.) 105 deg C, 2.) C₆H₆, MeOH, 0 deg C, 5 min

37: 92 percent / SmI₂, Ac₂O / tetrahydrofuran / 0.17 h / -78 °C

38: 1.) KOtBu, 2.) (PhSeO)2O, 3.) KOtBu

39: 76 percent / DMAP, Py / 16 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; dmap; palladium diacetate; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; borane-THF; tributylphosphine; collidinium p-toluene sulfonate; (PhSeO)2O; 4 A molecular sieve; naphthalenesulfonic acid; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; acetic anhydride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile; benzene;

DOI:10.1021/ja952692a

upstream raw materials:

C₄₁H₅₄N₂O₁₁SSi

acetic anhydride

C₃₅H₅₀O₉Si

triethylsilyl chloride

Downstream raw materials:

7-O-triethylsilyl-13-keto baccatin III

(13R)-13-deoxy-13-tert-butylperoxy-7-O-(triethylsilyl)baccatin III

13β-bromo-13-deoxy-7-O-(triethylsilyl)baccatin III

13-epi-7-O-(triethylsilyl)baccatin III

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