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254606

Sigma-Aldrich

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

96%

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Synonym(s):
α,β-Isopropylidene-L-glyceric acid methyl ester, Methyl α,β-isopropylidene-L-glycerate, Methyl 2,3-O-isopropylidene-L-glycerate
Empirical Formula (Hill Notation):
C7H12O4
CAS Number:
60456-21-5
Molecular Weight:
160.17
Beilstein:
4292352
MDL number:
MFCD00066526
UNSPSC Code:
12352005
PubChem Substance ID:
24855396
NACRES:
NA.22

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.)

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

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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.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

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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Annulation of 2-Oxoalkylidenetriphenylphosphoranes with enediones: A one-step synthesis of substituted cyclopentenones
Kitano H, et al.
Synthesis, 2002(06), 0739-0744 (2002)
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
Studies on the Synthesis of (−)-Gymnodimine. Subunit Synthesis and Coupling
White JD, et al.
The Journal of Organic Chemistry, 72(5), 1717-1728 (2007)
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

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