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345482

Sigma-Aldrich

Methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

98%

Synonym(s):

α,β-Isopropylidene-D-glyceric acid methyl ester, Methyl α,β-isopropylidene-D-glycerate, Methyl 2,3-O-isopropylidene-D-glycerate

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About This Item

Empirical Formula (Hill Notation):
C7H12O4
CAS Number:
52373-72-5
Molecular Weight:
160.17
Beilstein/REAXYS Number:
4292353
MDL number:
MFCD00066527
UNSPSC Code:
12352005
PubChem Substance ID:
24861325
NACRES:
NA.22

assay

98%

form

liquid

optical activity

[α]20/D +8.5°, c = 1.5 in acetone

refractive index

n20/D 1.426 (lit.)

bp

70-75 °C/10 mmHg (lit.)

density

1.106 g/mL at 25 °C (lit.)

SMILES string

COC(=O)[C@H]1COC(C)(C)O1

InChI

1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m1/s1

InChI key

DOWWCCDWPKGNGX-RXMQYKEDSA-N

Application

Methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate may be used as a starting material to synthesize (2R)-[1-2H2]-glycerol, a probe to study the stereochemistry of glycerol metabolism in Streptomyces cattleya. It may also be used to synthesize organic building blocks like (R)-2,3-dihydroxy-3-methylbutyl toluene-p-sulfonate and (2S,8R)-2-amino-8-[(R) 2,2-dimethyl-1,3-dioxolan-4-yl]-8-oxooctanoic acid.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. The stereochemical processing of glycerol.
Nieschalk J, et al.
Chemical Communications (Cambridge, England), 8, 799-800 (1997)
Synthesis of 2-amino-8-oxodecanoic acids (Aodas) present in natural hystone deacetylase inhibitors.
Rodriquez M, et al.
The Journal of Organic Chemistry, 71(1) (2006)
Synthesis of (24 R)-11a-(4-carboxybutyryloxy)-24, 25-dihydroxyvitamin D 3: a novel haptenic derivative producing antibodies of high affinity for (24 R)-24, 25-dihydroxyvitamin D 3.
Kobayashi N, et al.
J. Chem. Soc., Perkin Trans., 3, 269-275 (1994)

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