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

HRID 2086377

Reaction equation

HRID 2086377 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-271527c23872455486f25618a7eb7281
Source dataset
uspto-grants-2004_04
Patent number
US06723843B2

Linked notes

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