06357
(S)-4-Benzylthiazolidine-2-thione
≥95.0% (GC)
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About This Item
Empirical Formula (Hill Notation):
C10H11NS2
CAS Number:
Molecular Weight:
209.33
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Product Name
(S)-4-Benzylthiazolidine-2-thione, ≥95.0% (GC)
InChI key
SLDUGQISGRPGAW-VIFPVBQESA-N
SMILES string
S=C1N[C@H](CS1)Cc2ccccc2
InChI
1S/C10H11NS2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1
assay
≥95.0% (GC)
optical activity
[α]20/D -122±5°, c = 1% in chloroform
optical purity
enantiomeric ratio: ≥99:1 (LC)
functional group
phenyl
thioether
Quality Level
Application
A highly selective and efficient chiral auxiliary which can be directly reduced to its corresponding aldehyde and the chiral auxiliary by reductive cleavage with diisobutylaluminum hydride.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Velazquez. F.; Olivo, H. F.
Current Organic Chemistry, 6, 303-303 (2002)
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
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