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359068 Sigma-Aldrich

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

97%

Synonym: (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

  • CAS Number 37031-29-1

  • Empirical Formula (Hill Notation) C9H14O6

  • Molecular Weight 218.20

  •  Beilstein/REAXYS Number 15406

  •  MDL number MFCD00066218

  •  PubChem Substance ID 24862049

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Esters, Organic Building Blocks More...
assay   97%
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

Description

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.

Packaging

5, 25 mL in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
230 °F
Flash Point(C) 
110 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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