Octanoic Acid → isopropyl 6-O-octanoyl-alpha-D-glucopyranoside

HRID 1612917

반응식

HRID 1612917 반응식
[O:1]([CH:13]([CH3:15])[CH3:14])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:16](O)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C1C(CCCCC(N)=O)SSC1>CC(=O)CC>[C:16]([O:12][CH2:11][C@H:9]1[O:10][C@H:2]([O:1][CH:13]([CH3:15])[CH3:14])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

참가 물질

5

반응물 3

HCID 379Octanoic AcidHCID 863LipoamideHCID 179451isopropyl alpha-D-glucopyranoside

생성물 1

HCID 54267673isopropyl 6-O-octanoyl-alpha-D-glucopyranoside수율 70%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

To a stirred solution of isopropyl α-D-glucopyranoside (1.1 g, 5 mmol) and octanoic acid (0.9 g, 6.25 mmol) in 100 ml 2-butanone was added immobilized lipase (0.5 g Lipozyme™, see example 8). Stirring was continued at 60° C. for 48 hours. The enzyme was removed by filtration and the solvent was removed in vacuo followed by chromatography yielding 1.2 g (70%) of the product 1H NMR (400 MHz, CDCl3) δ: 0.88 (t, J=6.7 Hz, 3H); 1.19 (d, J=6.1 Hz, 3H); 1.24 (d, J=6.2 Hz, 3H); 1.28 (m, 8H); 1.62 (m, 2H); 2.34 (m, 2H); 3.35 (t, J=9.4 Hz, 1H); 3.50 (dd, J=4.0 and 9.5 Hz, 1H); 3.73 (t,J=9.3 Hz, 1 H); 3.85 (m, 1H); 3.92 (m, 1H) 4.35 (m, 2H); 4.96 (d, J=3.9 Hz, 1H).

후처리

  1. customThe enzyme was removed by filtration
  2. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-530966a8aba04cb4901aaefe1c536231
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05191071

연결된 노트

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