p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside
CAS No.:1352306-57-0
Molecular Formula:C₂₂H₂₂ClNO₆S
Molecular Weight:463.939
Hs Code.:

Synonyms:p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

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Chemical Property of p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

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Technology Process of p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

There total 4 articles about p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-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: 54.4%

: 1352306-53-6
p-chlorophenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

: 1352306-57-0
p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

: 1352306-54-7
p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-α-D-glucopyranoside

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 2h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.carres.2011.09.015

Reference yield:

: 1352306-48-9
p-chlorophenyl 2-amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

: 1352306-57-0
p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

: 1352306-54-7
p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydrogencarbonate / water; acetonitrile / 0 - 20 °C

2: sodium hydride / N,N-dimethyl-formamide / -10 - 20 °C

3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

With triethylsilane; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.carres.2011.09.015

Reference yield:

: 1352306-51-4
C₂₀H₁₈ClNO₅S

: 1352306-57-0
p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-β-D-glucopyranoside

: 1352306-54-7
p-chlorophenyl 2-acetamido-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / -10 - 20 °C

2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

With triethylsilane; boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2011.09.015