Lauric Acid → HCID 11100142, compound

HRID 1589776Notes

Reaction equation

[CH3:1][O:2][C@H:3]1[O:8][CH:7]([CH2:9][OH:10])[C@H:6]([OH:11])[C@@H:5]([OH:12])[C@@H:4]1[OH:13].O(C)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.O(C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.[C:40](O)(=[O:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]CC>>[C:40]([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:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

Reactant 4

HCID 3893Lauric Acid

HCID 64947methyl alpha-D-glucopyranoside

HCID 76607HCID 76607, compound

HCID 445238Methyl beta-D-glucopyranoside

Product 1

HCID 11100142HCID 11100142, compoundYield 79%

Procedure

Methyl-D-glucopyranoside (19.8 g, 0.10 mol, a 1:1 mixture of methyl α-(D)-glucopyranoside and methyl β-(D)-glucopyranoside, both Sigma Chemicals) was esterified with dodecanoic acid (31 g, 0.15 mol) by the procedure described in Example 1, using 3 g of an immobilized lipase (derived from Candida antarctica). The reaction was complete in 24 hours (HPLC showed>90% conversion) and the enzyme was removed by filtration. Purification by chromatography provided the title compound in a yield of 79% (30 g) as a crystalline powder, m,p. 70°-72° C.

Workup

custom(HPLC showed>90% conversion) and the enzyme was removed by filtration
customPurification by chromatography

Sources & evidence

ORD record: ord-c12b81d00fae49d1b1ab98a59fa03a42
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05200328

Reaction notes

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