2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

Base Information

Chemical Name:2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate
CAS No.:618115-57-4
Molecular Formula:C₂₉H₃₃Cl₃N₄O₁₄
Molecular Weight:767.958
Hs Code.:

Synonyms:2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

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Chemical Property of 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

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Technology Process of 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

There total 5 articles about 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-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: 95.0%

: 545-06-2
trichloroacetonitrile

: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,4aR,7R,8R,8aR)-7-azido-6-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester

: 618115-57-4
2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃;
DOI:10.1016/j.tetasy.2004.12.003

Reference yield:

: 4-pentenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-galactopyranoside

: 618115-57-4
2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / NBS / acetonitrile; H₂O

2: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; acetonitrile;
DOI:10.1016/S0008-6215(03)00323-9

Reference yield:

: (2S,4aR,7R,8R,8aR)-7-Azido-6-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 618115-57-4
2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl 2,2,2-trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / TMSOTf / CH₂Cl₂ / -45 - 20 °C

2: 100 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

3: 95 percent / DBU / CH₂Cl₂ / 0 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine trihydrofluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2004.12.003