2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS No.: 1384472-16-5
• Molecular Formula: C₂₂H₃₂O₈Si
• Molecular Weight: 452.577
• Mol file: 1384472-16-5.mol

Synonyms:2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

There total 3 articles about 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-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: 98.0%

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside + acetic anhydride (108-24-7) → 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside (1384472-16-5)

Guidance literature:

With dmap; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.6b01685

Reference yield:

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol (81336-89-2,81336-96-1,117252-95-6,132871-94-4,117252-72-9) → 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside (1384472-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3,5-trichloro-2,4,6-triazine / acetonitrile / 0.17 h / 60 °C / Sonication; Inert atmosphere

2: 1,3,5-trichloro-2,4,6-triazine / acetonitrile / 8 h / 90 °C / Sonication; Inert atmosphere

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile;

DOI:10.1039/c2ob25452b

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside (1384472-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3,5-trichloro-2,4,6-triazine / acetonitrile / 0.17 h / 60 °C / Sonication; Inert atmosphere

2: 1,3,5-trichloro-2,4,6-triazine / acetonitrile / 8 h / 90 °C / Sonication; Inert atmosphere

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile;

DOI:10.1039/c2ob25452b

upstream raw materials:

acetic anhydride

benzaldehyde dimethyl acetal

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

C₂₂H₃₄O₈Si