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

Base Information

Chemical Name:1,2-dihydrocinnamoyl-3-(N-hydrocinnamoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol
CAS No.:1473360-33-6
Molecular Formula:C₃₆H₄₃NO₁₀
Molecular Weight:649.738
Hs Code.:

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

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

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

There total 11 articles about 1,2-dihydrocinnamoyl-3-(N-hydrocinnamoyl-6'-amino-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: 82.0%

: 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

: 1473360-33-6
1,2-dihydrocinnamoyl-3-(N-hydrocinnamoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

Guidance literature:: With hydrogen; palladium(II) hydroxide; In tetrahydrofuran; isopropyl alcohol; for 8h;
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

: 1473360-33-6
1,2-dihydrocinnamoyl-3-(N-hydrocinnamoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

Guidance literature:: Multi-step reaction with 10 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: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.67 h / 0 °C

6: trimethylsilyl trifluoromethanesulfonate / diethyl ether / 2 h / 0 °C / Molecular sieve; Inert atmosphere

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

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

9: dmap; pyridine / 4 h / 20 °C

10: palladium(II) hydroxide; hydrogen / tetrahydrofuran; isopropyl alcohol / 8 h

With pyridine; methanol; dmap; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; palladium(II) hydroxide; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone;
DOI:10.1016/j.carres.2013.08.010

Reference yield:

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

: 1473360-33-6
1,2-dihydrocinnamoyl-3-(N-hydrocinnamoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol

Guidance literature:: Multi-step reaction with 5 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

5: palladium(II) hydroxide; hydrogen / tetrahydrofuran; isopropyl alcohol / 8 h

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