pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS No.: 920508-60-7
• Molecular Formula: C₂₇H₃₃NO₆
• Molecular Weight: 467.562

Synonyms:pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Chemical Property of pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

There total 4 articles about pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-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: 92.0%

pent-4-enyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (920508-59-4) + benzyl bromide (100-39-0) → pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (920508-60-7)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1002/hlca.200690234

Reference yield:

4-pentenyl 2-acetamido-2-deoxy-α-D-glucopyranoside (262363-68-8) → pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (920508-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 11.1 g / TsOH*H₂O / acetonitrile / 15 h / 20 °C / pH 3 - 4

2: 92 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide / 20 h / 20 °C

With barium dihydroxide; toluene-4-sulfonic acid; barium(II) oxide; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200690234

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → pent-4-enyl N-acetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (920508-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1: TsOH*H₂O / 24 h / 90 °C

2: 11.1 g / TsOH*H₂O / acetonitrile / 15 h / 20 °C / pH 3 - 4

3: 92 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide / 20 h / 20 °C

With barium dihydroxide; toluene-4-sulfonic acid; barium(II) oxide; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200690234

upstream raw materials:

pent-4-enyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

benzyl bromide

4-pentenyl 2-acetamido-2-deoxy-α-D-glucopyranoside

n-Pent-4-enyl alcohol

Downstream raw materials:

pent-4-enyl N,N-diacetyl-2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

pent-4-enyl (methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->4)-N,N-diacetyl-2-amino-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

pent-4-enyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-N,N-diacetyl-2-amino-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

pent-4-enyl N,N-diacetyl-2-amino-3,6-O-dibenzyl-2-deoxy-α-D-glucopyranoside

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