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163457

Sigma-Aldrich

(+)-Dimethyl L-tartrate

99%

Synonym(s):

L-(+)-Tartaric acid dimethyl ester

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About This Item

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Treatment of dimethyl (+)-L-tartrate with sulfur tetrafluoride.
Burmakov AI, et al.
Journal of Fluorine Chemistry, 19(2), 151-161 (1981)

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