O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate
• CAS No.: 120449-25-4
• Molecular Formula: C₂₉H₃₀Cl₃NO₅
• Molecular Weight: 578.92
• Mol file: 120449-25-4.mol

Synonyms:O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate

Chemical Property of O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate

There total 3 articles about O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate 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%

2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose (33639-75-7,86795-38-2,101802-96-4,127875-50-7,134311-86-7,134312-04-2) + trichloroacetonitrile (545-06-2) → O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate (120449-25-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h; Ambient temperature;

Reference yield:

Phosphoric acid dibenzyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (120449-27-6,120449-28-7,128473-01-8,128473-02-9) → 2,2,2-Trichloro-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (83866-10-8,103368-09-8,120449-25-4,120449-26-5,120703-59-5,136633-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / 10percent Pd/C / tetrahydrofuran; ethyl acetate

2: K₂CO₃

With hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/S0040-4039(01)80315-4

Reference yield:

2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose (33639-75-7,86795-38-2,101802-96-4,127875-50-7,134311-86-7,134312-04-2) + trichloroacetonitrile (545-06-2) → 2,2,2-Trichloro-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (83866-10-8,103368-09-8,120449-25-4,120449-26-5,120703-59-5,136633-04-0)

Guidance literature:

With potassium carbonate; Yield given;

DOI:10.1016/S0040-4039(01)80315-4

upstream raw materials:

2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose

trichloroacetonitrile

Phosphoric acid dibenzyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester

Downstream raw materials:

tert-Butyldimethylsilyl O-(2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-<(2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranosyl)-(1-2)>-3-O-benzyl-β-D-xylopyranoside

tert-Butyldimethylsilyl O-(2,3,4-Tri-O-benzyl-6-deoxy-β-D-glucopyranosyl)-(1-2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-<(2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranosyl)-(1-2)>-3-O-benzyl-β-D-xylopyranoside

C₅₅H₅₄O₁₃

C₃₇H₄₄O₅