3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Base Information

• Chemical Name: 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester
• CAS No.: 214678-60-1
• Molecular Formula: C₂₉H₄₂O₇SSi
• Molecular Weight: 562.8
• Mol file: 214678-60-1.mol

Synonyms:3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Chemical Property of 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

There total 4 articles about 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl 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: 96.0%

trimethyl 3-(phenylsulfonyl)orthopropionate (38435-08-4) + Trifluoro-methanesulfonic acid (4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (214678-59-8) → 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester (214678-60-1)

Guidance literature:

With n-butyllithium; Ambient temperature;

DOI:10.1016/S0040-4039(98)01562-7

Reference yield: 50.0%

trimethyl 3-(phenylsulfonyl)orthopropionate (38435-08-4) + Trifluoro-methanesulfonic acid (4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (214678-59-8) → C38H62O7Si2 + 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester (214678-60-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; Ambient temperature;

DOI:10.1016/S0040-4039(98)01562-7

Reference yield:

(4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol (214678-58-7) → 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester (214678-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 0.5 h / -10 °C

2: 50 percent / nBuLi, HMPA / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane;

DOI:10.1016/S0040-4039(98)01562-7

upstream raw materials:

trimethyl 3-(phenylsulfonyl)orthopropionate

Trifluoro-methanesulfonic acid (4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol

Downstream raw materials:

(R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one