3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

Base Information

Chemical Name:3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol
CAS No.:909100-00-1
Molecular Formula:C₃₇H₄₂ClNO₁₆
Molecular Weight:792.191
Hs Code.:

Synonyms:3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

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Chemical Property of 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

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Technology Process of 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

There total 3 articles about 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol 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: 71.0%

: 909099-99-6
4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

: 74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9
2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

: 909100-00-1
3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.25h; cooling;
DOI:10.1016/j.carres.2006.05.004

Reference yield:

: 3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

: 909100-00-1
3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1: K₂CO₃

2: 71 percent / 4 A MS; TMSOTf / CH₂Cl₂ / 0.25 h / cooling

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In dichloromethane;
DOI:10.1016/j.carres.2006.05.004

Reference yield:

: 138381-83-6
4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

: 909100-00-1
3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1: 25 percent / 2,6-lutidine; Et₃N / CH₂Cl₂ / 3.5 h / 0 °C

2: 71 percent / 4 A MS; TMSOTf / CH₂Cl₂ / 0.25 h / cooling

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;
DOI:10.1016/j.carres.2006.05.004