3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

Base Information

Chemical Name:3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene
CAS No.:176257-50-4
Molecular Formula:C₃₀H₃₃N₃O₄
Molecular Weight:499.61
Hs Code.:

Synonyms:3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

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Chemical Property of 3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

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Technology Process of 3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

There total 5 articles about 3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene 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:

: Methanesulfonic acid (2R,3R,4R,5S,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

: 176257-50-4
3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 20h; Yield given;
DOI:10.1021/ja9525622

Reference yield:

: 100-39-0
benzyl bromide

: 176257-50-4
3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 16 h

2: 38 percent / trimethylsilyl triflate (TMSOTf) / acetonitrile / 16 h

3: Et₃N / CH₂Cl₂ / 18 h

4: NaN₃ / dimethylformamide / 20 h / 90 °C

With sodium azide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja9525622

Reference yield:

: 82614-11-7
[(2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(prop-2-en-1-yl)oxan-2-yl]methanol

: 176257-50-4
3-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1-propene

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 18 h

2: NaN₃ / dimethylformamide / 20 h / 90 °C

With sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9525622