Dichloromethane → HCID 86760330, compound

HRID 857967Notes

Reaction equation

HRID 857967 reaction equation
[CH3:1][C:2]([Si:5]([CH3:59])([CH3:58])[O:6][C@@H:7]([C@@H:45]([CH3:57])[CH2:46][O:47]CC1C=CC(OC)=CC=1)[C@@H:8]([CH3:44])[CH2:9][N:10]([C:12](=[O:43])[C@H:13]([CH3:42])[C@@H:14]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C@H:15]([CH3:33])[C@@H:16]([O:23]CC1C=CC(OC)=CC=1)[C@@H:17]([CH3:22])/[CH:18]=[CH:19]\[CH:20]=[CH2:21])[CH3:11])([CH3:4])[CH3:3].C(Cl)Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O>[CH3:1][C:2]([Si:5]([CH3:58])([CH3:59])[O:6][C@@H:7]([C@@H:45]([CH3:57])[CH2:46][OH:47])[C@@H:8]([CH3:44])[CH2:9][N:10]([C:12](=[O:43])[C@H:13]([CH3:42])[C@@H:14]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])[CH3:37])[C@H:15]([CH3:33])[C@@H:16]([OH:23])[C@@H:17]([CH3:22])/[CH:18]=[CH:19]\[CH:20]=[CH2:21])[CH3:11])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86760331HCID 86760331, compound

Product 1

HCID 86760330HCID 86760330, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of 1,2,4-trideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-1-[[(2R,3S,4R,5S,6S,7Z)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]methylamino]-5-O-[(4-methoxyphenyl)methyl]-2,4-dimethyl-L-arabinitol (1.9 g, 2.2 mmol), CH2Cl2 (40 mL), and H2O (1 mL) at room temperature, is added 2,3-dichloro-5,6-Dicyano-1,4-benzoquinone (DDQ), (2.53 g, 11.1 mmol). After stirring at room temperature for 10 min, the reaction mixture is purified by column chromatography on silica gel with hexane/EtOAc (90/10) to give the desired product (1.15 g, 82.6%) as a white solid.

Workup

  1. customthe reaction mixture is purified by column chromatography on silica gel with hexane/EtOAc (90/10)

Sources & evidence

ORD record
ord-ff317f41e6c247d084e385af928c39e8
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

Loading…