2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside
• CAS No.: 152771-13-6
• Molecular Formula: C₃₈H₅₂O₁₀Si
• Molecular Weight: 696.91
• Mol file: 152771-13-6.mol

Synonyms:2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside

Chemical Property of 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside

There total 10 articles about 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-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: 83.0%

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-6-O-(2-methoxypropyl)-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside → 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside (152771-13-6)

Guidance literature:

With acetic acid; at 60 ℃; for 0.75h;

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

Reference yield:

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (152771-11-4) → 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside (152771-13-6)

Guidance literature:

Multi-step reaction with 4 steps

1: p-TsOH / 48 h / Ambient temperature

2: 1,2-dichloro-ethane / 60 °C

3: Bu₃SnH, AIBN / toluene / Heating

4: 80percent aq. AcOH / 60 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; In 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo00127a042

Reference yield:

{(3aR,4R,6S,7aR)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl}-methanol → 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside (152771-13-6)

Guidance literature:

With acetic acid; at 60 ℃; Yield given;

DOI:10.1021/jo00127a042

upstream raw materials:

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

C₄₇H₆₆O₁₂S₂Si

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Downstream raw materials:

2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(3,6-di-O-benzoyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside