p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside
• CAS No.: 727991-12-0
• Molecular Formula: C₂₁H₂₄Cl₃NO₈S
• Molecular Weight: 556.848

Synonyms:p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Chemical Property of p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

There total 8 articles about p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside 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: 90.0%

p-tolyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-galactopyranoside (949489-05-8) + trifluoroacetyl chloride (76-02-8) → p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (727991-12-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02271

Reference yield: 77.0%

para-thiocresol (106-45-6) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-galactopyranoside → p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (727991-12-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 25 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jacs.9b06830

Reference yield:

para-thiocresol (106-45-6) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-galactopyranoside → p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (727991-12-0) + p-methylphenyl 2-deoxy-2-trichloroacetamido-3,4,6-tri-O-acetyl-1-thio-α-D-galactopyranoside

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ja0484045

upstream raw materials:

para-thiocresol

D-(+)-galactosamine hydrochloride

1,3,4,6-Tetra-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-α/β-D-galactopyranose

p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

Downstream raw materials:

methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

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