Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Base Information

Chemical Name:Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester
CAS No.:107195-06-2
Molecular Formula:C₃₃H₅₆O₅Si₂
Molecular Weight:588.976
Hs Code.:

Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Synonyms:Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

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Chemical Property of Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Chemical Property:

Purity/Quality:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

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Technology Process of Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

There total 14 articles about Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester 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: 97.0%

: 107195-05-1
Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-5-(2-hydroxy-ethyl)-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 107195-06-2
Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 5h;
DOI:10.1016/S0040-4039(00)84394-4

Reference yield:

: 928-91-6
(Z)-4-hexenol

: 107195-06-2
Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 54 percent / PCC / CH₂Cl₂ / 2 h / 0 - 25 °C

2: 1.) Mg / 2.) THF, 0deg C, 1.5 h

3: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 °C

4: pentane / 25 °C / Irradiation

5: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 °C

6: 94 percent / NaBH₄ / methanol / 0.25 h / 25 °C

7: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 °C

8: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 °C / 760 Torr

9: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 °C

11: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 °C

12: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC

13: 97 percent / imidazole / dimethylformamide / 5 h / 25 °C

With 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; mercury(II) diacetate; hydrogen; ozone; magnesium; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(00)84394-4

Reference yield:

4-hexyn-1-ol: 928-93-8
4-hexyn-1-ol

: 107195-06-2
Benzoic acid (3S,3aR,5S,6S,7S,8S,8aR,9S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Guidance literature:: Multi-step reaction with 14 steps

1: H₂ / Pd/CaCO₃, (Lindlar),quinoline / pentane / 25 °C / 517.1 - 2068.6 Torr

2: 54 percent / PCC / CH₂Cl₂ / 2 h / 0 - 25 °C

3: 1.) Mg / 2.) THF, 0deg C, 1.5 h

4: 97 percent / DMAP, Et₃N / dimethylformamide / 10 h / 25 °C

5: pentane / 25 °C / Irradiation

6: 71 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.25 h / 25 °C

7: 94 percent / NaBH₄ / methanol / 0.25 h / 25 °C

8: 93 percent / MnO₂ / CH₂Cl₂ / 24 h / 25 °C

9: 99 percent / H₂ / 5percent Pd/C / diethyl ether / 11 h / 25 °C / 760 Torr

10: 95 percent / DMAP, Et₃N / dimethylformamide / 36 h / 46 - 50 °C

12: 72 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 °C

13: 1.) O₃, 2.) NaBH₄ / 1. MeOH, CH₂Cl₂, -78 gradC; 2. -78 gradC to 25 gradC

14: 97 percent / imidazole / dimethylformamide / 5 h / 25 °C

With 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; mercury(II) diacetate; hydrogen; ozone; magnesium; triethylamine; pyridinium chlorochromate; quinoline; palladium on activated charcoal; Lindlar's catalyst; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(00)84394-4