Trimethylsilyl triflate → Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside

HRID 2086377

반응식

HRID 2086377 반응식
[C:1]([O:4][C@H:5]([C@H:8]([C@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=O)C)C=O)(=[O:3])[CH3:2].[CH2:28]([S:30][Si](C)(C)C)[CH3:29].FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(Cl)Cl>[C:25]([O:24][C@@H:23]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:8]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:9][C@H:10]1[S:30][CH2:28][CH3:29])(=[O:27])[CH3:26]

참가 물질

5

반응물 3

HCID 65367Trimethylsilyl triflateHCID 81232D-galactose, 2,3,4,5,6-pentaacetateHCID 2733426(Ethylthio)trimethylsilane

생성물 1

HCID 10572588Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of galactose pentaacetate (38.00 g, 97.43 mmol), (ethylthio)trimethylsilane (19.60 g, 146.15 mmol) and trimethylsilyl trifluoromethanesulfonate (23.60 g, 106.20 mmol) in CH2Cl2 (150 ml) was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (150 ml) and washed with 1M Na2CO3 solution (300 ml), water (300 ml), dried over MgSO4 and concentrated. The residue was crystallised from hexane/diisopropyl ether 1:1 (v/v) to give ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (34.00 g, 89%).

후처리

  1. washwashed with 1M Na2CO3 solution (300 ml), water (300 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was crystallised from hexane/diisopropyl ether 1:1 (v/v)

출처 및 근거

ORD 기록
ord-271527c23872455486f25618a7eb7281
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06723843B2

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