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59539

Sigma-Aldrich

(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol

≥97.0% (sum of enantiomers, GC)

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Synonym(s):
(+)-2,3-O-Isopropylidene-L-threitol, (4S,5S)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane
Empirical Formula (Hill Notation):
C7H14O4
CAS Number:
Molecular Weight:
162.18
Beilstein/REAXYS Number:
1280797
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

≥97.0% (sum of enantiomers, GC)

form

solid

optical activity

[α]20/D +3.0±0.5°, c = 5% in ethanol

bp

92-94 °C/0.1 mmHg (lit.)

mp

46-50 °C

SMILES string

CC1(C)O[C@@H](CO)[C@H](CO)O1

InChI

1S/C7H14O4/c1-7(2)10-5(3-8)6(4-9)11-7/h5-6,8-9H,3-4H2,1-2H3/t5-,6-/m0/s1

InChI key

INVRLGIKFANLFP-WDSKDSINSA-N

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This Item
59490241806265004
Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

bp

92-94 °C/0.1 mmHg (lit.)

bp

-

bp

72-73 °C/8 mmHg (lit.)

bp

-

mp

46-50 °C

mp

213-216 °C (lit.)

mp

-

mp

193-195 °C (lit.)

form

solid

form

-

form

liquid

form

-

optical activity

[α]20/D +3.0±0.5°, c = 5% in ethanol

optical activity

[α]20/D −116±2°, c = 1% in ethyl acetate

optical activity

[α]20/D −13.7°, neat

optical activity

[α]19/D −62.6°, c = 1 in chloroform

Application

(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol can be used:
  • As a key intermediate for the preparation of (6Z)-cis-9S,10R-epoxy-nonadecene, a female sex pheromone of elm spanworm.
  • To prepare a chiral diphosphite ligand by reacting with phosphorochloridite using excess of NEt3. 

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)


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Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hubner)(Lepidoptera: Geometridae)
MaGee DI, et al.
Tetrahedron, 67(29), 5329-5338 (2011)
Modular chiral diphosphite derived from l-tartaric acid. Applications in metal-catalyzed asymmetric reactions
Rosas-Hern'andez A, et al.
J. Mol. Catal. A: Chem., 328(1-2), 68-75 (2010)

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