Hexadecanoic acid, ethenyl ester → 4-nitrophenyl 6-O-palmitoyl-alpha-D-glucopyranoside

HRID 1275530

반응식

HRID 1275530 반응식
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([O:10][C@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]2[OH:21])[CH:2]=1.[C:22](OC=C)(=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CC(C)=O>[C:22]([O:18][CH2:17][C@H:15]1[O:16][C@H:11]([O:10][C:3]2[CH:2]=[CH:1][C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=2)[C@H:12]([OH:21])[C@@H:13]([OH:20])[C@@H:14]1[OH:19])(=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

참가 물질

4

반응물 2

HCID 69658Hexadecanoic acid, ethenyl esterHCID 92969p-nitrophenyl alpha-D-glucopyranoside

생성물 1

HCID 538237954-nitrophenyl 6-O-palmitoyl-alpha-D-glucopyranoside수율 84.9%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

In 40 ml of acetone were suspended 0.3 g (1 mmol) of 4-nitrophenyl-α-D-glucopyranoside (manufactured by Tokyo Kasei Ind., Ltd.) as marketed, 0.85 g (3 mmol) of vinyl palmitate and 30 mg of Lipase B, and the suspension was reacted in a shaking apparatus at 25° C. for 1 day. After the enzyme was filtered off, the solvent was concentrated to afford a crude product in a white wax form, which was purified by silica gel chromatography (5% methanol-dichloromethane) to give 0.458 g of 4-nitrophenyl 6-O-palmitoyl-α-D-glucopyranoside in a white wax form. Yield 81%

후처리

  1. filtrationAfter the enzyme was filtered off
  2. concentrationthe solvent was concentrated
  3. customto afford a crude product in a white wax form, which
  4. customwas purified by silica gel chromatography (5% methanol-dichloromethane)

출처 및 근거

ORD 기록
ord-ba148674400b429699974ad338e6c017
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162614

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