Water → 4,5-Diacetoxy-6-acetoxymethyl-2-(2-acetyl-thiophen-3-yloxy)-tetrahydro-pyran-3-yl acetate

HRID 1445322Notes

Reaction equation

HRID 1445322 reaction equation
[OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:9])[CH3:8].[C:10]([O:13][CH:14]1[CH:19]([O:20][C:21](=[O:23])[CH3:22])[CH:18]([O:24][C:25](=[O:27])[CH3:26])[CH:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][CH:15]1Br)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].O>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[C:10]([O:13][CH:14]1[CH:19]([O:20][C:21](=[O:23])[CH3:22])[CH:18]([O:24][C:25](=[O:27])[CH3:26])[CH:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][CH:15]1[O:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:9])[CH3:8])(=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 102932alpha-D-Galactopyranosyl bromide, tetraacetateHCID 133523522-Acetyl-3-hydroxythiophene

Product 1

HCID 219612284,5-Diacetoxy-6-acetoxymethyl-2-(2-acetyl-thiophen-3-yloxy)-tetrahydro-pyran-3-yl acetate

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2 g of 1-(3-hydroxy-thiophen-2-yl)-ethanone were dissolved in 120 ml of dichloromethane and stirred with 6.4 g of 4,5-diacetoxy-6-acetoxymethyl-2-bromotetrahydropyran-3-yl acetate, 1.4 g of benzyltributylammonium chloride, 6.4 g of potassium carbonate and 1.2 ml of water at 22° C. for 20 h. Insoluble constituents were removed by filtration, the filtrate was concentrated and the crude product mixture was purified by column chromatograph (SiO2, ethyl acetate/n-heptane=1:1). The product with the molecular weight of 472.5 (C20H24O11S), MS (Cl): 473 (M+H+) was obtained

Workup

  1. customInsoluble constituents were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe crude product mixture was purified by column chromatograph (SiO2, ethyl acetate/n-heptane=1:1)
  4. customThe product with the molecular weight of 472.5 (C20H24O11S), MS (Cl): 473 (M+H+) was obtained

Sources & evidence

ORD record
ord-64b3963be3514a219d29fa86775286c3
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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