tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside
• CAS No.: 637763-62-3
• Molecular Formula: C₃₀H₄₀Cl₃NO₇Si
• Molecular Weight: 661.095

Synonyms:tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside

Chemical Property:

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Technology Process of tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside

There total 2 articles about tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-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: 99.0%

acetic anhydride (108-24-7) + tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside (637763-48-5) → tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside (637763-62-3)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol035887t

Reference yield:

N-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trichloro-acetamide → tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside (637763-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / triethylsilane; trifluoromethanesulfonic acid; trifluoromethanesulfonic acid anhydride / CH₂Cl₂ / 1.67 h / 0 - 20 °C

2: 99 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With triethylsilane; dmap; trifluorormethanesulfonic acid; trifluoromethanesulfonic acid anhydride; In dichloromethane;

DOI:10.1021/ol035887t

Reference yield:

tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-4-O-acetyl-2-trichloroacetamido-β-D-glucopyranoside (637763-62-3) → Acetic acid (2R,3S,4R,5R)-4-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-3-yl ester

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol035887t

upstream raw materials:

acetic anhydride

tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

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