methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester

Base Information

• Chemical Name: methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester
• CAS No.: 888954-88-9
• Molecular Formula: C₂₃H₃₈O₈SSi
• Molecular Weight: 502.701
• Mol file: 888954-88-9.mol

Synonyms:methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester

Chemical Property of methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester

There total 5 articles about methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl 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: 90.0%

methanesulfonyl chloride (124-63-0) + 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol (106445-04-9) → methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester (888954-88-9)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; cooling;

DOI:10.1055/s-2006-926369

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester (888954-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / imidazole / CH₂Cl₂ / 1.5 h / 0 °C

2: 90 percent / Et₃N / CH₂Cl₂ / 1 h / cooling

With 1H-imidazole; triethylamine; In dichloromethane;

DOI:10.1055/s-2006-926369

Reference yield:

benzyl bromide (100-39-0) → methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester (888954-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / aq. NaOH; Bu₄NBr / CH₂Cl₂ / 12 h / 20 °C

2: 89 percent / aq. AcOH / 12 h / 20 °C

3: 89 percent / imidazole / CH₂Cl₂ / 1.5 h / 0 °C

4: 90 percent / Et₃N / CH₂Cl₂ / 1 h / cooling

With 1H-imidazole; sodium hydroxide; tetrabutylammomium bromide; acetic acid; triethylamine; In dichloromethane;

DOI:10.1055/s-2006-926369

upstream raw materials:

methanesulfonyl chloride

1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

[1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl]carbamic acid benzyl ester

2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol

[2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethoxy]-tert-butyl dimethylsilane