Dichloromethane → 2,4-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-[(4-methoxyphenyl)methyl]-2,4-dimethyl-L-lyxose

HRID 857961Notes

Reaction equation

HRID 857961 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C@H:8]([CH3:24])[C@H:9]([C@@H:20]([CH3:23])[CH2:21][OH:22])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([CH3:4])[CH3:3].CCN(CC)CC.C(Cl)Cl>CS(C)=O.CCOCC>[CH3:1][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][CH2:7][C@H:8]([CH3:24])[C@@H:9]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C@@H:20]([CH3:23])[CH:21]=[O:22])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 11222796HCID 11222796, compound

Product 1

HCID 111117042,4-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-[(4-methoxyphenyl)methyl]-2,4-dimethyl-L-lyxoseYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,4-dideoxy-1-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-[(4-methoxyphenyl)methyl]-2,4-dimethyl-L-arabinitol (10.77 g, 28.19 mmol), DMSO (30 mL), NEt3 (11.39 g, 112.76 mmol) and methylene chloride is cooled to −10° C., and treated with SO3-Pyr (13.45 9, 84.58 mmol)in DMSO (60 mL) over 40 min. After additional 2 h at 0° C., the mixture is diluted with ether (300 mL), washed with 1 M aqueous NaHSO4 (100 mL), brine (100 mL), and concentrated. Flash chromatography (5% ethyl acetate in hexane) gives the desired compound (9 g, 84%) as a colorless oil.

Workup

  1. washwashed with 1 M aqueous NaHSO4 (100 mL), brine (100 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-12c0a3629d154503bc712c271149ab76
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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