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163457

Sigma-Aldrich

(+)-Dimethyl L-tartrate

99%

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Synonym(s):
L-(+)-Tartaric acid dimethyl ester
Linear Formula:
[-CH(OH)CO2CH3]2
CAS Number:
608-68-4
Molecular Weight:
178.14
Beilstein:
1726256
EC Number:
210-166-8
MDL number:
MFCD00064437
UNSPSC Code:
12352108
PubChem Substance ID:
24849749
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

optical activity

[α]22/D +21°, c = 2.5 in H2O

optical purity

ee: ≥99% (GLC)

bp

163 °C/23 mmHg (lit.)

mp

57-60 °C (dec.) (lit.)

density

1.238 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C6H10O6/c1-11-5(9)3(7)4(8)6(10)12-2/h3-4,7-8H,1-2H3/t3-,4-/m1/s1

InChI key

PVRATXCXJDHJJN-QWWZWVQMSA-N

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Application

(+)-Dimethyl L-tartrate can react with sulfur tetrafluoride to form dimethyl meso-2,3-difluorosuccinate.
It may be used in the synthesis of the following chiral ligands for use in asymmetric synthesis:
  • (2R, 3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol
  • (-)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane (PYDIPHOS)
  • (4R,5R)-α,α,α′,α′-2,2-hexaphenyl-4,5-dimethanol-1,3-dioxolane

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Synthesis of (2R, 3R)-1, 4-dimethoxy-1, 1, 4, 4-tetraphenyl-2, 3-butanediol: A new C2-symmetric vicinal diol from dimethyl L-tartrate.
Nakayama K and Rainier JD.
Tetrahedron, 46(12), 4165-4170 (1990)
(-)-(4S, 5R)-4-(2-pyridyl)-5-(diphenylphosphino) methyl-2, 2-dimethyl-1, 3-dioxolane a new chiral ligand for enantioselective catalysis.
Chelucci G, et al.
Tetrahedron Asymmetry, 5(3), 299-302 (1994)
Treatment of dimethyl (+)-L-tartrate with sulfur tetrafluoride.
Burmakov AI, et al.
Journal of Fluorine Chemistry, 19(2), 151-161 (1981)
Synthesis and structure of (4R, 5R)-a, a, a', a'-2, 2-hexaphenyl-4, 5-dimethanol-1, 3-dioxolane.
Irurre J, et al.
Tetrahedron Asymmetry, 3(12), 1591-1596 (1992)

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