2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Base Information

Chemical Name:2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
CAS No.:1333393-50-2
Molecular Formula:C₃₂H₃₉N₃O₁₀
Molecular Weight:625.676
Hs Code.:

Synonyms:2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

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Chemical Property of 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

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Technology Process of 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

There total 4 articles about 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 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:

: 1333393-48-8
p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 1333393-64-8
2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 1333393-50-2
2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Guidance literature:: p-tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-thio-β-D-galactopyranoside; With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-formamide; In dichloromethane; at -10 ℃; for 1.5h; Molecular sieve;

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose; In dichloromethane; at -10 ℃; for 5h; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/anie.201100076

Reference yield:

: p-tolyl 4,6-O-benzylidene-2-deoxy-2-azido-1-thio-α-D-galactopyranoside

: 1333393-64-8
2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 1333393-50-2
2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C

2.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-formamide / dichloromethane / 1.5 h / -10 °C / Molecular sieve

2.2: 5 h / -10 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201100076

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 1333393-64-8
2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 1333393-50-2
2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C

3.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-formamide / dichloromethane / 1.5 h / -10 °C / Molecular sieve

3.2: 5 h / -10 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1002/anie.201100076