dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 1616627-99-6
• Molecular Formula: C₂₃H₃₄Cl₃NO₆Si
• Molecular Weight: 554.971

Synonyms:dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

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Technology Process of dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 5 articles about dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-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: 66.0%

benzaldehyde dimethyl acetal (1125-88-8) + dimethylthexylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside (1616627-97-4) → dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1616627-99-6)

Guidance literature:

dimethylthexylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside; With sodium methylate; In methanol; for 4h;

In methanol;

benzaldehyde dimethyl acetal; With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/jacs.8b08857

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + C16H30Cl3NO6Si → dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1616627-99-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2014.05.007

Reference yield:

dimethylthexylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside (1616627-97-4) → dimethylthexylsilyl 2-trichloroacetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1616627-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate; methanol / 12 h

2: toluene-4-sulfonic acid / acetonitrile / 3 h / 20 °C

With methanol; sodium methylate; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1016/j.carres.2014.05.007

upstream raw materials:

dimethylthexylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

benzaldehyde dimethyl acetal

1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose

Downstream raw materials:

dimethylthexylsilyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside

dimethylthexylsilyl 6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside

benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate

benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate

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