3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate
• CAS No.: 205593-86-8
• Molecular Formula: C₂₉H₂₉Cl₃N₄O₅
• Molecular Weight: 619.932

Synonyms:3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate

Chemical Property of 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate

Chemical Property:

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Technology Process of 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate

There total 8 articles about 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-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: 84.0%

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose (79781-69-4) + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate (205593-86-8)

Guidance literature:

With potassium carbonate; In dichloromethane; at 30 ℃; for 6h;

DOI:10.1021/jo971727h

Reference yield:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose (79781-69-4) + trichloroacetonitrile (545-06-2) → O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate (94715-55-6) + 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate (205593-86-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h; Overall yield = 83 %; Overall yield = 1.24 g;

DOI:10.3762/bjoc.14.258

Reference yield:

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate (205593-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium cerium (IV) nitrate; sodium azide / acetonitrile / 6 h / -25 °C / Inert atmosphere

2: water / acetone / 0.25 h / 120 °C / Microwave irradiation

3: potassium carbonate / dichloromethane / 5 h / 0 °C / Inert atmosphere

With sodium azide; ammonium cerium (IV) nitrate; water; potassium carbonate; In dichloromethane; acetone; acetonitrile;

DOI:10.1021/jacs.9b06830

upstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

trichloroacetonitrile

D-galactose pentaacetate

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

2-((2S,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-pyridine

2-pyridyl 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-thio-α-D-galactopyranoside

N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridin-2-ylsulfanyl)-tetrahydro-pyran-3-yl]-acetamide

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