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254606

Sigma-Aldrich

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

96%

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C7H12O4
Numero CAS:
60456-21-5
Peso molecolare:
160.17
Beilstein:
4292352
Numero MDL:
MFCD00066526
Codice UNSPSC:
12352005
ID PubChem:
24855396
NACRES:
NA.22

Saggio

96%

Forma fisica

liquid

Attività ottica

[α]20/D −8.5°, c = 1.5 in acetone

Purezza ottica

ee: ≥96.0% (GLC)

Indice di rifrazione

n20/D 1.425 (lit.)

P. eboll.

84-86 °C/15 mmHg (lit.)

Densità

1.106 g/mL at 25 °C (lit.)

Stringa SMILE

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
DOWWCCDWPKGNGX-YFKPBYRVSA-N

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Applicazioni

(−)-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.

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

172.4 °F - closed cup

Punto d’infiammabilità (°C)

78 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificati d'analisi (COA)

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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
White JD, et al.
The Journal of Organic Chemistry, 72(5), 1717-1728 (2007)
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
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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