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About This Item
Empirical Formula (Hill Notation):
C6H11NS2
CAS Number:
Molecular Weight:
161.29
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
assay
≥98.0%
form
solid
optical activity
[α]20/D -37±3°, c = 1 in chloroform
optical purity
ee: ≥99:1 (LC)
mp
69-71 °C
SMILES string
CC(C)[C@H]1CSC(=S)N1
InChI
1S/C6H11NS2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m1/s1
InChI key
CWIZUGZKLJDJLE-RXMQYKEDSA-N
Application
(S)-4-Isopropylthiazolidine-2-thione may be used as a chiral auxiliary for the stereochemical induction at the phosphorus atom during the diastereoselective synthesis of aryloxy phosphoramidate prodrugs of 3′-deoxy-2′,3′-didehydrothymidine monophosphate (d4TMP).
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_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Certificates of Analysis (COA)
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Diastereoselective synthesis of aryloxy phosphoramidate prodrugs of 3'-deoxy-2', 3'-didehydrothymidine monophosphate.
Roman CA, et al.
Journal of Medicinal Chemistry, 53(21), 7675-7681 (2010)
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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