1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

Base Information

Chemical Name:1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol
CAS No.:1383450-17-6
Molecular Formula:C₅₇H₆₁NO₁₀
Molecular Weight:920.112
Hs Code.:

Synonyms:1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

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Chemical Property of 1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

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Technology Process of 1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

There total 7 articles about 1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol 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: 77.0%

: 1383450-05-2
3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

: 645-45-4
hydrocinnamic acid chloride

: 1383450-17-6
1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 4h;
DOI:10.1016/j.carres.2012.04.005

Reference yield:

: 479252-05-6
((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol

: 1383450-17-6
1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; triethylamine / dichloromethane / 5 h / 20 °C

2.1: sodium azide / N,N-dimethyl-formamide / 60 °C

3.1: N-iodo-succinimide / diethyl ether / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 72 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

5.1: triphenylphosphine / tetrahydrofuran; water / 5 h / 50 °C

6.1: dmap / pyridine / 4 h / 20 °C

With dmap; N-iodo-succinimide; sodium azide; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2012.04.005

Reference yield:

: 1383449-95-3
p-tolyl 2,3,4-tri-O-benzyl-6-O-p-tosyl-1-thio-β-D-glucopyranoside

: 1383450-17-6
1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium azide / N,N-dimethyl-formamide / 60 °C

2.1: N-iodo-succinimide / diethyl ether / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 72 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

4.1: triphenylphosphine / tetrahydrofuran; water / 5 h / 50 °C

5.1: dmap / pyridine / 4 h / 20 °C

With dmap; N-iodo-succinimide; sodium azide; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2012.04.005