benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

Base Information

Chemical Name:benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside
CAS No.:157001-34-8
Molecular Formula:C₂₃H₂₅ClO₇
Molecular Weight:448.9
Hs Code.:

Synonyms:benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

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Technology Process of benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

There total 1 articles about benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-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: 86.0%

: (4aR,6S,7R,8R,8aR)-6-Benzyloxy-8-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 541-88-8
Chloroacetic anhydride

: 157001-34-8
benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; for 4h;
DOI:10.1016/0008-6215(94)80062-6

Reference yield: 94.0%

: 157001-34-8
benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

: 157001-35-9
benzyl 2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

Guidance literature:: With acetic acid; at 90 ℃; for 0.75h;
DOI:10.1016/0008-6215(94)80062-6

Reference yield:

: 157001-34-8
benzyl 4,6-O-benzylidene-2-O-chloroacetyl-3-O-methyl-α-D-glucopyranoside

: (2S,4aR,6S,7R,8R,8aR)-6-Benzyloxy-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / 80percent aq. AcOH / 0.75 h / 90 °C

2: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

3: 1.) piperidine thiocarbamide, 2.) methyl chloroacetate, / 1.) MeOH, RT, 36 h, 2.) MeOH, 24 h

With piperidine thiocarbamide; boron trifluoride diethyl etherate; acetic acid; methyl chloroacetate; In dichloromethane;
DOI:10.1016/0008-6215(94)80062-6