2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate
• CAS No.: 230620-34-5
• Molecular Formula: C₁₆H₁₇Cl₃N₄O₅
• Molecular Weight: 451.694
• Mol file: 230620-34-5.mol

Synonyms:2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property of 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate

There total 3 articles about 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl 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: 69.0%

trichloroacetonitrile (545-06-2) + 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-D-galactopyranose → 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate (230620-34-5)

Guidance literature:

With sodium hydride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1139/v99-056

Reference yield:

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside (147254-13-5) → 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate (230620-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 97 percent / dimethylformamide / 0.25 h / 0 °C

2.1: Bu₄NF / CH₂Cl₂; tetrahydrofuran / 0.17 h / -25 °C

3.1: 69 percent / NaH / CH₂Cl₂ / 1 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: desilylation / 3.1: Addition;

DOI:10.1139/v99-056

Reference yield:

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside (230620-33-4) → 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate (230620-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₄NF / CH₂Cl₂; tetrahydrofuran / 0.17 h / -25 °C

2: 69 percent / NaH / CH₂Cl₂ / 1 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; 1: desilylation / 2: Addition;

DOI:10.1139/v99-056

upstream raw materials:

trichloroacetonitrile

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

Downstream raw materials:

1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribitol

1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 5-O-p-methoxybenzyl-2,3,4-tri-O-benzyl-L-ribitol

(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-D-ribityl-5-phosphate

(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribityl-5-phosphate