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Merck
CN

359068

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

97%

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

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About This Item

Empirical Formula (Hill Notation):
C9H14O6
CAS Number:
37031-29-1
Molecular Weight:
218.20
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24862049
MDL number:
MFCD00066218
Beilstein/REAXYS Number:
15406

Key Documents

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Product Name

(−)-Dimethyl 2,3-O-isopropylidene-L-tartrate, 97%

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

SMILES string

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

InChI key

ROZOUYVVWUTPNG-PHDIDXHHSA-N

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.)

functional group

ester
ether
ketal

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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.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7230
BCBF9551V
1451851V
1451851
1384349

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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)
Tetrahedron Letters, 31, 7179-7179 (1990)
Angewandte Chemie (International Edition in English), 30, 99-99 (1991)
Organic Syntheses, 68, 92-92 (1990)
The total synthesis of (+)-migrastatin.
Gaul C, et al.
Journal of the American Chemical Society, 125(20), 6042-6043 (2003)
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