methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Base Information

Chemical Name:methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
CAS No.:866890-34-8
Molecular Formula:C₄₃H₅₁N₃O₁₂
Molecular Weight:801.891
Hs Code.:

methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

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Chemical Property of methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

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Technology Process of methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

There total 1 articles about methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 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:

: (3aR,4R,5aR,8S,9aS,9bS)-4-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2,2-dibutyl-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene

: 187404-16-6
benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate

: (3S,4aS,4bS,6S,8aR,10R,10aR)-10-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-cyclohexylmethyl-6-phenyl-hexahydro-1,4,5,7,9-pentaoxa-phenanthren-2-one

: 866890-34-8
methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: With cesium fluoride; In 1,2-dimethoxyethane; at 20 ℃; for 1.25h;
DOI:10.1080/07328300500176312

Reference yield:

: 866890-34-8
methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: (S)-2-[(2S,4aR,6R,7R,8R,8aS)-6-((2S,4aR,6R,7R,8R,8aR)-7-Amino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3-cyclohexyl-propionic acid benzyl ester

Guidance literature:: With pyridine; 1.3-propanedithiol; triethylamine; In water; at 20 ℃; for 4.5h; pH=9 - 10;
DOI:10.1080/07328300500176312

Reference yield:

: 866890-34-8
methyl {4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)-2-cyclohexylethyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: (S)-2-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-3-cyclohexyl-propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1,3-propanedithiol; pyridine; triethylamine / H₂O / 4.5 h / 20 °C / pH 9 - 10

2.1: 105 mg / pyridine / 16 h / 20 °C

3.1: ethanethiol; TsOH / CH₂Cl₂; methanol / 24 h / 20 °C

3.2: 72 percent / pyridine / 72 h / 20 °C

4.1: hydrogen / palladium on carbon / methanol / 16 h

5.1: sodium methanolate / methanol / 24 h / 20 °C

With pyridine; 1.3-propanedithiol; hydrogen; sodium methylate; toluene-4-sulfonic acid; triethylamine; ethanethiol; palladium on activated charcoal; In methanol; dichloromethane; water; 5.1: Zemplen deacetylation;
DOI:10.1080/07328300500176312