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359068

Sigma-Aldrich

(−)-Dimethyl 2,3-O-isopropylidene-L-tartrate

97%

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Synonym(s):
(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester, Dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
Empirical Formula (Hill Notation):
C9H14O6
CAS Number:
37031-29-1
Molecular Weight:
218.20
Beilstein:
15406
MDL number:
MFCD00066218
UNSPSC Code:
12352005
PubChem Substance ID:
24862049
NACRES:
NA.22

Assay

97%

form

liquid

optical activity

[α]20/D −54°, neat

refractive index

n20/D 1.439 (lit.)

bp

150 °C/19 mmHg (lit.)

density

1.190 g/mL at 20 °C (lit.)

SMILES string

COC(=O)[C@@H]1OC(C)(C)O[C@H]1C(=O)OC

InChI

1S/C9H14O6/c1-9(2)14-5(7(10)12-3)6(15-9)8(11)13-4/h5-6H,1-4H3/t5-,6-/m1/s1

InChI key

ROZOUYVVWUTPNG-PHDIDXHHSA-N

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Application

(-)-Dimethyl 2,3-O-isopropylidene-L-tartrate may be used as a starting material in the total synthesis of (+)-migrastatin and also in the synthesis of a structural analog of S-ribosylhomocysteinase (LuxS), which acts as a potent competitive inhibitor against LuxS.
Valuable building block for TADDOL chiral auxiliaries, dipyridine ligands, and threitols.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Design and synthesis of substrate and intermediate analogue inhibitors of S-ribosylhomocysteinase.
Shen G, et al.
Journal of Medicinal Chemistry, 49(10), 3003-3011 (2006)
Angewandte Chemie (International Edition in English), 30, 99-99 (1991)
Organic Syntheses, 68, 92-92 (1990)
Tetrahedron Letters, 31, 7179-7179 (1990)
The Journal of Organic Chemistry, 57, 6825-6825 (1992)
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