(S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanal → 3-(1-Oxo-2-(R)-methyl-3-(R)-hydroxy-4-(S)-methyl-5-t-butyldimethylsiloxypentyl)-4-(R)-(phenylmethyl)-2-oxazolidinone

HRID 1729458Notes

Reaction equation

HRID 1729458 reaction equation
[O:1]=[C:2]([N:5]1[C@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][C:6]1=[O:17])[CH2:3][CH3:4].[CH3:18][C@@H:19]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:20]=[O:21]>>[O:1]=[C:2]([N:5]1[C@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][C:6]1=[O:17])[C@H:3]([CH3:4])[C@H:20]([OH:21])[C@@H:19]([CH3:18])[CH2:22][O:23][Si:24]([C:27]([CH3:29])([CH3:28])[CH3:30])([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 10241965(S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanalHCID 10966403(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone

Product 1

HCID 538292083-(1-Oxo-2-(R)-methyl-3-(R)-hydroxy-4-(S)-methyl-5-t-butyldimethylsiloxypentyl)-4-(R)-(phenylmethyl)-2-oxazolidinone

Procedure

This material is prepared from (R)-3-(1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone and 2-(S)-methyl-3-t-butyldimethylsiloxypropanal following the method of Evans and Gage, as described in Org. Syn., Vol. 68, 19xx, p. 83.

Sources & evidence

ORD record
ord-f641894474f242d3bf4f1488823031b8
Source dataset
uspto-grants-1994_07
Patent number
US05332807

Reaction notes

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