O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate
• CAS No.: 129753-04-4
• Molecular Formula: C₁₉H₂₀Cl₃NO₈
• Molecular Weight: 496.729

Synonyms:O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Chemical Property of O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Chemical Property:

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Technology Process of O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

There total 2 articles about O-(2,3-di-O-acetyl-4,6-O-benzylidene-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: 77.0%

trichloroacetonitrile (545-06-2) + 2,3-di-O-acetyl-4,6-O-benzylidene-D-galactopyranose → O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (129753-04-4)

Guidance literature:

With sodium hydride; In dichloromethane; for 0.333333h; Ambient temperature;

Reference yield:

4,6-O-benzylidene-1,2,3-tris-O-acetyl-D-galactopyranoside (243136-79-0) → O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (129753-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / 2-aminoethanol; EtOAc / 20 °C

2: 71 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

With potassium carbonate; ethanolamine; ethyl acetate; In dichloromethane; 1: Deacetylation / 2: Addition;

DOI:10.1016/S0008-6215(99)00022-1

Reference yield: 94.0%

O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (129753-04-4) + benzyl O-(2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside → benzyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-O-(2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1...

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; for 0.5h; Ambient temperature;

DOI:10.1021/jo9608073

upstream raw materials:

trichloroacetonitrile

4,6-O-benzylidene-1,2,3-tris-O-acetyl-D-galactopyranoside

Downstream raw materials:

Benzyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

tert-Butyldimethylsilyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Acetic acid (2S,4aR,6S,7R,8S,8aS)-8-acetoxy-6-[(2R,3S,4R,5R,6R)-6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

5-azido-3-oxapentyl (2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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