2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside
• CAS No.: 152770-95-1
• Molecular Formula: C₂₇H₃₆O₆S₂Si
• Molecular Weight: 548.797
• Mol file: 152770-95-1.mol

Synonyms:2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

Chemical Property of 2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

There total 1 articles about 2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside 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:

carbon disulfide (75-15-0,12122-00-8) + (2R,4aR,6R,7R,8S,8aS)-7-Benzyloxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol + methyl iodide (74-88-4) → 2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (152770-95-1)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/0008-6215(93)84028-5

Reference yield: 98.0%

2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (152770-95-1) → 2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-ribo-hexopyranoside (152770-96-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1016/0008-6215(93)84028-5

Reference yield:

2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (152770-95-1) → 2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-β-D-ribo-hexopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Bu₃SnH, AIBN / toluene / Heating

2: 75 percent / NaBH₃CN, ether. HCl, mol. sieves 3 Angstroem / tetrahydrofuran / 0.08 h

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; sodium cyanoborohydride; In tetrahydrofuran; toluene;

DOI:10.1016/0008-6215(93)84028-5

upstream raw materials:

carbon disulfide

methyl iodide

Downstream raw materials:

2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-ribo-hexopyranoside

2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside