3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

Base Information

Chemical Name:3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside
CAS No.:1262208-42-3
Molecular Formula:C₃₉H₄₅NO₉
Molecular Weight:671.788
Hs Code.:

Synonyms:3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

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Chemical Property of 3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

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Technology Process of 3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

There total 7 articles about 3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside 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: 69.0%

: 1262208-39-8
3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-α-D-mannopyranoside

: 2746-25-0
p-Methoxybenzyl bromide

: 1262208-42-3
3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

Guidance literature:: 3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 1h; Molecular sieve; Reflux;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; at 60 ℃; regioselective reaction;

Reference yield:

: 1236190-06-9
3-(benzyloxycarbonyl)aminopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

: 1262208-42-3
3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium methylate / methanol / 12 h / 20 °C

1.2: Dowex H⁺

2.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C

3.1: water / methanol / 6 h / 20 °C

4.1: 18-crown-6 ether; sodium hydroxide / tetrahydrofuran; water / 72 h / 20 °C

5.1: acetic acid / water / 12 h / 50 °C

6.1: di(n-butyl)tin oxide / toluene / 1 h / Molecular sieve; Reflux

6.2: 12 h / 60 °C / Molecular sieve

With 18-crown-6 ether; water; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; sodium hydroxide; In tetrahydrofuran; methanol; water; acetone; toluene;
DOI:10.1021/ol1026188

Reference yield:

: 1262208-34-3
3-(benzyloxycarbonyl)aminopropyl 2,3-O-isopropylidene-α-D-mannopyranoside 12

: 1262208-42-3
3-(benzyloxycarbonyl)aminopropyl 4,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 18-crown-6 ether; sodium hydroxide / tetrahydrofuran; water / 72 h / 20 °C

2.1: acetic acid / water / 12 h / 50 °C

3.1: di(n-butyl)tin oxide / toluene / 1 h / Molecular sieve; Reflux

3.2: 12 h / 60 °C / Molecular sieve

With 18-crown-6 ether; di(n-butyl)tin oxide; acetic acid; sodium hydroxide; In tetrahydrofuran; water; toluene;
DOI:10.1021/ol1026188