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384313

Sigma-Aldrich

(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate

98%

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Synonym(s):
(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester, Dimethyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
Empirical Formula (Hill Notation):
C9H14O6
CAS Number:
37031-30-4
Molecular Weight:
218.20
Beilstein:
3548490
MDL number:
MFCD00040504
UNSPSC Code:
12352005
PubChem Substance ID:
24863661
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

optical activity

[α]20/D +54°, neat

refractive index

n20/D 1.439 (lit.)

bp

80-82 °C/0.1 mmHg (lit.)

density

1.19 g/mL at 25 °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-/m0/s1

InChI key

ROZOUYVVWUTPNG-WDSKDSINSA-N

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General description

(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate is a chiral reagent used in organic synthesis. It is prepared by the reaction-rectification process from D -tartrate, and 2,2-dimethoxypropane.{138]

Application

(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate can be used as a starting material for the synthesis of:
  • Deuterated 1-deoxy-D-xylose.
  • C-terminal peptide -oxo-aldehydes using Fmoc solid-phase peptide synthesis methodology (SPPS).
  • Bis-Weinreb amide, a key intermediate for the preparation of myo-inositol analog via ring-closing metathesis.

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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A new linker for the synthesis of C-terminal peptide ?-oxo-aldehydes
Fruchart J-S, et al.
Tetrahedron Letters, 40(34), 6225-6228 (1999)
Rosemary M Conrad et al.
Organic letters, 4(8), 1359-1361 (2002-04-13)
Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. A readily available bis-Weinreb amide of D-tartrate served as a key intermediate. [reaction: see text]
Highly efficient and versatile synthesis of isotopically labelled 1-deoxy-D-xylulose
Piel J and Boland W
Tetrahedron Letters, 38(36), 6387-6390 (1997)
Angewandte Chemie (International Edition in English), 30, 99-99 (1991)
Organic Syntheses, 68, 92-92 (1990)
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