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08416

Sigma-Aldrich

(S)-4-Benzyloxazolidine-2-thione

≥97.0%

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About This Item

Empirical Formula (Hill Notation):
C10H11NOS
CAS Number:
145588-94-9
Molecular Weight:
193.27
MDL number:
MFCD06658221
UNSPSC Code:
12352005
PubChem Substance ID:
329748581
NACRES:
NA.22

Quality Level

100

assay

≥97.0%

optical purity

enantiomeric excess: ≥98.0% (HPLC)

mp

63-67 °C

functional group

phenyl

SMILES string

S=C1N[C@H](CO1)Cc2ccccc2

InChI

1S/C10H11NOS/c13-10-11-9(7-12-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,13)/t9-/m0/s1

InChI key

WJSUXYCBZFLXIK-VIFPVBQESA-N

Application

Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries
A highly selective and efficient chiral auxiliary[1] which can be directly reduced to its corresponding aldehyde and the chiral auxiliary by reductive cleavage with diisobutylaluminum hydride.[2]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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M T Crimmins et al.
Organic letters, 2(6), 775-777 (2001-02-07)
[formula: see text] Asymmetric aldol additions using chlorotitanium enolates of thiazolidinethione propionates proceed with high diastereoselectivity for the "Evans" or "non-Evans" syn product depending on the nature and amount of the base used. With (-)-sparteine as the base, selectivities of
Velazquez. F.; Olivo, H. F.
Current Organic Chemistry, 6, 303-303 (2002)

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