Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-2-yl ester
• CAS No.: 219740-15-5
• Molecular Formula: C₄₀H₅₆O₇SSi
• Molecular Weight: 709.032

Synonyms:

Chemical Property of Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-2-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-2-yl ester

There total 9 articles about Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-2-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: 91.0%

phenyllithium (591-51-5) + C34H50O7SSi (219740-11-1) → Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-2-yl ester (219740-15-5)

Guidance literature:

DOI:10.1016/S0960-894X(98)00540-X

Reference yield:

(S)-1-Hydroxy-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enecarbaldehyde (162084-46-0) → Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-2-yl ester (219740-15-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) tBuMgCl

2: Et₃N, H₂O

3: 1.) MeB(OH)2, 2.) TiCl₄, 3.) HF, KF

4: Et₃N

5: 91 percent / DMAP

7: LiAl(O^tBu)3H

8: 91 percent

With dmap; potassium fluoride; dihydroxy-methyl-borane; hydrogen fluoride; tert-butylmagnesium chloride; water; titanium tetrachloride; lithium tri-t-butoxyaluminum hydride; triethylamine;

DOI:10.1016/S0960-894X(98)00540-X

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Benzoic acid (1S,2S,4S,9R,10R,13S)-9-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-1,4,13-trihydroxy-4,12,15,15-tetramethyl-10-phenylsulfanyl-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-2-yl ester (219740-15-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N

2: 91 percent / DMAP

4: LiAl(O^tBu)3H

5: 91 percent

With dmap; lithium tri-t-butoxyaluminum hydride; triethylamine;

DOI:10.1016/S0960-894X(98)00540-X

upstream raw materials:

phenyllithium

C₃₄H₅₀O₇SSi

tert-butyldimethylsilyl chloride

(S)-1-Hydroxy-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enecarbaldehyde

Downstream raw materials:

C₆₄H₈₅NO₁₁SSi₂

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