5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Name:5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:1169693-80-4
Molecular Formula:C₃₃H₃₆N₄O₇
Molecular Weight:600.671
Hs Code.:

Synonyms:5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 6 articles about 5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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%

: 1169693-77-9
5-azidopentyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

: 1169693-80-4
5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: 5-azidopentyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside; With sodium methylate; In methanol; at 20 ℃; for 2h;

With Amberlite IR-120; In methanol;
DOI:10.1016/j.tetasy.2009.02.028

Reference yield: 75.0%

: 170220-11-8
5-azido-1-pentanol

: 807361-23-5
p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

: 1169693-80-4
5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: 5-azido-1-pentanol; p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 1h; Molecular sieve;

With N-iodo-succinimide; trifluorormethanesulfonic acid; at -20 ℃; for 2h;
DOI:10.1021/ja409097c

Reference yield:

: p-tolyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 1169693-80-4
5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / methanol

2.1: sodium hydride / N,N-dimethyl-formamide / 4 h

3.1: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / 0 °C

4.1: dichloromethane / 1 h / 20 °C / Molecular sieve

4.2: 2 h / -20 °C

With triethylsilane; sodium methylate; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja409097c