5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

Base Information

Chemical Name:5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside
CAS No.:243136-77-8
Molecular Formula:C₂₆H₃₂N₄O₇
Molecular Weight:512.563
Hs Code.:

Synonyms:5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

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Chemical Property of 5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

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Technology Process of 5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

There total 1 articles about 5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside 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: 85.0%

: 100-39-0
benzyl bromide

: N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(2-Azido-ethoxy)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

: 243136-77-8
5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

Guidance literature:: With barium dihydroxide; N,N-dimethyl-formamide; barium(II) oxide; In dichloromethane; for 1h; Heating;
DOI:10.1016/S0008-6215(99)00022-1

Reference yield: 60.0%

: 243136-77-8
5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

: 243136-78-9
5-azido-3-oxapentyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopranoside

Guidance literature:: With 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 0.25h;
DOI:10.1016/S0008-6215(99)00022-1

Reference yield:

: 243136-77-8
5-azido-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopranoside

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

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / NaBH₃CN; 3A molecular sieves / tetrahydrofuran / 0.25 h / 20 °C

2: 58 percent / silver trifluoromethanesulfonate; ethyldiisopropylamine; 4A molecular sieves / CH₂Cl₂ / 20 °C

With 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Etherification;
DOI:10.1016/S0008-6215(99)00022-1