Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-2-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-2-yl ester
• CAS No.: 832724-36-4
• Molecular Formula: C₃₄H₅₄O₈SSi
• Molecular Weight: 650.949
• Mol file: 832724-36-4.mol

Synonyms:Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-2-yl ester

Chemical Property of Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-2-yl ester

There total 1 articles about Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-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: 92.0%

methanesulfonyl chloride (124-63-0) + (1S,2R,4S,5S,9R,11S,12S)-5-(tert-Butyl-dimethyl-silanyloxy)-11,12-dihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.04,9]pentadecan-3-one (350715-45-6) → Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-2-yl ester (832724-36-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/jo048289g

Reference yield: 65.0%

Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-2-yl ester (832724-36-4) → (Z)-(1S,2R,4S,5S,9R,12R)-5-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.04,9]pentadec-10-en-3-one (832724-37-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 100 ℃; for 32h;

DOI:10.1021/jo048289g

Reference yield:

Methanesulfonic acid (1S,2S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-2-yl ester (832724-36-4) → C33H50O6Si

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / DBU / benzene / 32 h / 100 °C

2: 84 percent / tert-butyl hydroperoxide; VO(acac)2 / CH₂Cl₂ / 24 h

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; benzene;

DOI:10.1021/jo048289g

upstream raw materials:

methanesulfonyl chloride

(1S,2R,4S,5S,9R,11S,12S)-5-(tert-Butyl-dimethyl-silanyloxy)-11,12-dihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

Downstream raw materials:

(Z)-(1S,2R,4S,5S,9R,12R)-5-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadec-10-en-3-one