Decanoic Acid → methyl 6-O-decanoyl-D-glucopyranoside

HRID 1589777노트

반응식

HRID 1589777 반응식
[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].[C:14](O)(=[O:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[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:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

참가 물질

3

반응물 2

HCID 2969Decanoic AcidHCID 76607Methyl glucoside

생성물 1

HCID 11100142methyl 6-O-decanoyl-D-glucopyranoside수율 59%

실험 절차

Methyl-D-glucopyranoside (a 2:3 mixture of the α- and β-anomers) (24 g, 0.12 mol, prepared according to Example 6) was esterified with decanoic acid (43 g, 0.25 mol) by the procedure described in Example 1 using 2.4 g of an immobilized lipase (derived from Candida antarctica). After 17 hours the enzyme was removed by filtration (at 80° C.) HPLC analysis of the crude product showed 77% of the title compound, 15% diesters and 8% methyl-D-glucopyranoside. Part of the crude product was purified by chromatography, yielding 39.4 g (59%) of the title compound which was identified by NMR spectroscopy.

후처리

  1. custom(24 g, 0.12 mol, prepared according to Example 6)
  2. customAfter 17 hours the enzyme was removed by filtration (at 80° C.) HPLC analysis of the crude product
  3. customPart of the crude product was purified by chromatography

출처 및 근거

ORD 기록
ord-4b246a95891e4d66a44cc2bc032b1850
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05200328

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