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

Base Information

Chemical Name:1,2-dihydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol
CAS No.:1473360-26-7
Molecular Formula:C₅₇H₆₁NO₁₀
Molecular Weight:920.112
Hs Code.:

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

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

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

There total 11 articles about 1,2-dihydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-mannopyranosyl)-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: 75.0%

: 1473360-18-7
3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

: 645-45-4
hydrocinnamic acid chloride

: 1473360-26-7
1,2-dihydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

Guidance literature:: With pyridine; dmap; at 20 ℃; for 4h;
DOI:10.1016/j.carres.2013.08.010

Reference yield:

: 210170-40-4
1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-mannopyranoside

: 1473360-26-7
1,2-dihydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

Guidance literature:: Multi-step reaction with 8 steps

1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C

2: methanol; sodium methylate / 0.5 h / pH 9

3: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C

4: water; N-Bromosuccinimide / acetone / 1 h

5: trimethylsilyl trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 16 h / 0 °C / Molecular sieve; Inert atmosphere

6: toluene-4-sulfonic acid / methanol / 2 h

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

8: dmap; pyridine / 4 h / 20 °C

With pyridine; methanol; dmap; N-Bromosuccinimide; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.carres.2013.08.010

Reference yield:

: 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside

: 1473360-26-7
1,2-dihydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

Guidance literature:: Multi-step reaction with 4 steps

1: trimethylsilyl trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 16 h / 0 °C / Molecular sieve; Inert atmosphere

2: toluene-4-sulfonic acid / methanol / 2 h

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

4: dmap; pyridine / 4 h / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; water; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.carres.2013.08.010