Lauric Acid → HCID 18650857, compound

HRID 1589779Notes

Reaction equation

HRID 1589779 reaction equation
[CH3:1][O:2][C@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13].[C:14](O)(=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>>[C:14]([O:10][CH2:9][C@H:7]1[O:8][CH:3]([O:2][CH3:1])[C@H:4]([OH:13])[C@@H:5]([OH:12])[C@@H:6]1[OH:11])(=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 3893Lauric AcidHCID 64947methyl alpha-D-glucopyranoside

Product 1

HCID 18650857HCID 18650857, compound

Procedure

After 18 hours methyl-α-D-glucopyranoside (64 g, 0.33 mol, prepared according to example 6), dodecanoic acid (90 g, 0.45 mol) and 6 g lipase were added. After additional 22 hours the enzyme was removed by filtration and the product was worked up by short path distillation according to example 1, yielding a crude product containing 84% 6-O-dodecanoyl-D-glucopyranoside 9% methyl-D-glucoside and 7% diesters Part of the product was purified by chromatography and the identity of the title compound (being a ca 1:1 mixture of the anomers) was confirmed by NMR spectroscopy.

Workup

  1. customAfter additional 22 hours the enzyme was removed by filtration
  2. distillationthe product was worked up by short path distillation

Sources & evidence

ORD record
ord-ab41a5b688bd49d4bc6adc30ef6953af
Source dataset
uspto-grants-1993_04
Patent number
US05200328

Reaction notes

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