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254606

(−)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Name: (−)-Methyl (<I>S</I>)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
Brand: ALDRICH

96%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₇H₁₂O₄

CAS Number:

60456-21-5

Molecular Weight:

160.17

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24855396

MDL number:

MFCD00066526

Beilstein/REAXYS Number:

4292352

Assay:

96%

Form:

liquid

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Properties

Quality Level

200

assay

96%

form

liquid

optical activity

[α]20/D −8.5°, c = 1.5 in acetone

optical purity

ee: ≥96.0% (GLC)

refractive index

n20/D 1.425 (lit.)

bp

84-86 °C/15 mmHg (lit.)

density

1.106 g/mL at 25 °C (lit.)

functional group

ester, ether, ketal

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-/m0/s1

InChI key

DOWWCCDWPKGNGX-YFKPBYRVSA-N

Description

Application

(−)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate can be used:

As a chiral building block to make the key tetrahydrofuran subunit of (−)-gymnodimine, a marine algal toxin.
To prepare an enedione by reacting with dimethyl methylphosphonate, BuLi, and phenylglyoxal, which in turn is used to synthesize cyclopentenone derivatives.
As a starting material for the preparation of (S)-4,5-dihydroxy-2,3-pentanedione (DPD), a precursor for autoinducer (AI)-2 in bacteria.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

172.4 °F - closed cup

flash_point_c

78 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Annulation of 2-Oxoalkylidenetriphenylphosphoranes with enediones: A one-step synthesis of substituted cyclopentenones

Kitano H, et al.

Synthesis, 2002(06), 0739-0744 (2002)

Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling.

James D White et al.

The Journal of organic chemistry, 72(5), 1717-1728 (2007-02-01)

Two principal subunits of the marine algal toxin (-)-gymnodimine were synthesized. A trisubstituted tetrahydrofuran representing C10-C18 of the toxin was prepared via a highly stereoselective iodine-mediated cyclization of an acyclic alkene bearing a bis-2,6-dichlorobenzyl (DCB) ether. The formation of a

Chemical synthesis of (S)-4,5-dihydroxy-2,3-pentanedione, a bacterial signal molecule precursor, and validation of its activity in Salmonella typhimurium.

Sigrid C J De Keersmaecker et al.

The Journal of biological chemistry, 280(20), 19563-19568 (2005-03-26)

We describe an original, short, and convenient chemical synthesis of enantiopure (S)-4,5-dihydroxy-2,3-pentanedione (DPD), starting from commercial methyl (S)-(-)-2,2-dimethyl-1,3-dioxolane-4-carboxylate. DPD is the precursor of autoinducer (AI)-2, the proposed signal for bacterial interspecies communication. AI-2 is synthesized by many bacterial species in

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Global Trade Item Number

SKU	GTIN
254606-5G	04061837392825