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254606

Sigma-Aldrich

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

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
Beilstein/REAXYS Number:
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_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (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)
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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