Chloroform → HCID 54015903, compound

HRID 1583821Notes

Reaction equation

HRID 1583821 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][S:21]([CH3:24])(=[O:23])=[O:22])[O:7][C@@H:6]1[S:25][C:26](=N)N)(=[O:3])[CH3:2].C(Br)[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(Cl)(Cl)Cl>CCOC(C)=O>[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][S:21]([CH3:24])(=[O:23])=[O:22])[O:7][C@@H:6]1[S:25][CH2:26][CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 98116BromomethylstyreneHCID 12805518HCID 12805518, compound

Product 1

HCID 54015903HCID 54015903, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound is prepared from 2-S-(2,3,4-tri-O-acetyl-6-O-methylsulfonyl-α-D-mannopyranosyl)-2-thiopseudourea and cinnamyl bromide in the usual manner. The desired product is isolated by column chromatography (silica gel; CHCl3 --EtOAc, 92:8, v/v) in 65-70% yield: m.p. 111°-113° C. (ether-petroleum ether); [α]D27 +175±1.1° (C 1.0, chloroform).

Sources & evidence

ORD record
ord-4a8c3477ee4742078881bbef35bfb1b1
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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