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

Base Information

Chemical Name:Benzoic acid (3S,3aR,5R,6S,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester
CAS No.:107163-93-9
Molecular Formula:C₂₈H₄₂O₄Si
Molecular Weight:470.725
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 24 articles about Benzoic acid (3S,3aR,5R,6S,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-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: 72.0%

: 107164-01-2
Benzoic acid (3S,3aR,5R,7R,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-8-methyl-6-oxo-octahydro-3a,7-methano-azulen-9-yl ester

: 107163-93-9,107164-04-5
Benzoic acid (3S,3aR,5R,6R,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

: 107163-93-9,107164-04-5
Benzoic acid (3S,3aR,5R,6S,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(00)84394-4

Reference yield: 72.0%

: 107164-01-2
Benzoic acid (3S,3aR,5R,7R,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-8-methyl-6-oxo-octahydro-3a,7-methano-azulen-9-yl ester

: 107163-93-9,107164-04-5
Benzoic acid (3S,3aR,5R,6R,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

: 107163-93-9,107164-04-5
Benzoic acid (3S,3aR,5R,6S,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(00)84394-4

Reference yield:

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

: 107163-93-9,107164-04-5
Benzoic acid (3S,3aR,5R,6R,7S,8S,8aR,9S)-5-allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-8-methyl-octahydro-3a,7-methano-azulen-9-yl ester

Guidance literature:: Multi-step reaction with 11 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: 27 percent / NaBH₄, CeCl₃ / methanol / 3 h / -78 °C

With dmap; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; mercury(II) diacetate; hydrogen; 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