6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 125164-10-5
• Molecular Formula: C₃₁H₃₂Cl₃NO₇
• Molecular Weight: 636.957
• Mol file: 125164-10-5.mol

Synonyms:6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Chemical Property of 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

There total 3 articles about 6-O-acetyl-2,3,4-tri-O-benzyl-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: 100.0%

6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranoside (88567-49-1,88567-50-4,93361-01-4,101802-94-2,101802-97-5,127875-38-1) + trichloroacetonitrile (545-06-2) → 6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranosyl trichloroacetimidate (125164-10-5,125164-11-6,143826-39-5,143826-40-8)

Guidance literature:

With potassium carbonate; In dichloromethane; for 4.5h;

DOI:10.1016/S0040-4020(01)88221-1

Reference yield:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5) → 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (125164-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / benzylamine / 3 h / 20 °C

2: 75 percent / NaH / CH₂Cl₂ / 3 h / 20 °C

With sodium hydride; benzylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2003.10.047

Reference yield:

1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (10548-46-6) → 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (125164-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / CF₃COOH / 5 h / 20 °C

2: 90 percent / benzylamine / 3 h / 20 °C

3: 75 percent / NaH / CH₂Cl₂ / 3 h / 20 °C

With sodium hydride; benzylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2003.10.047

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranoside

trichloroacetonitrile

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose

Downstream raw materials:

(S)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester

(S)-3-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(tert-butyl-diphenyl-silanyloxy)-heptadecanoic acid tert-butyl ester

(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

(S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester