(3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

Base Information

• Chemical Name: (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol
• CAS No.: 225788-81-8
• Molecular Formula: C₂₁H₃₄O₇SSi
• Molecular Weight: 458.648
• Mol file: 225788-81-8.mol

Synonyms:

Chemical Property of (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

There total 3 articles about (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 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:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol (225788-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 15 h / 35 °C

2: 1.) n-BuLi / 1.) THF, hexane, from -60 deg C to 0 deg C, 0.5 h, 2.) THF, hexane, a) -60 deg C, 3 h, b) -35 deg C, 2 h

With 1H-imidazole; n-butyllithium; In N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570360236

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol (225788-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 15 h / 35 °C

2: 1.) n-BuLi / 1.) THF, hexane, from -60 deg C to 0 deg C, 0.5 h, 2.) THF, hexane, a) -60 deg C, 3 h, b) -35 deg C, 2 h

With 1H-imidazole; n-butyllithium; In N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570360236

Reference yield:

methylphenylsulfonate (3112-85-4) + 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone (75467-36-6) → (3aR,4R,6R,6aR)-4-Benzenesulfonylmethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol (225788-81-8)

Guidance literature:

With n-butyllithium; Yield given; Multistep reaction; 1.) THF, hexane, from -60 deg C to 0 deg C, 0.5 h, 2.) THF, hexane, a) -60 deg C, 3 h, b) -35 deg C, 2 h;

DOI:10.1002/jhet.5570360236

upstream raw materials:

methylphenylsulfonate

5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone

2,3-O-isopropylidene-D-ribonic-γ-lactone

tert-butyldimethylsilyl chloride