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480819

Sigma-Aldrich

(R)-(+)-Glycidol

97%, optical purity ee: 98% (GLC)

Synonym(s):

(R)-(+)-Oxirane-2-methanol

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About This Item

Empirical Formula (Hill Notation):
C3H6O2
CAS Number:
57044-25-4
Molecular Weight:
74.08
Beilstein:
79782
EC Number:
404-660-4
MDL number:
MFCD00074873
UNSPSC Code:
12352005
PubChem Substance ID:
24871720
NACRES:
NA.22

Assay

97%

optical activity

[α]23/D +15°, neat

optical purity

ee: 98% (GLC)

impurities

<3% dichloromethane

refractive index

n20/D 1.43 (lit.)

bp

56-57 °C/11 mmHg (lit.)

density

1.116 g/mL at 20 °C (lit.)

storage temp.

−20°C

SMILES string

OC[C@@H]1CO1

InChI

1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2/t3-/m1/s1

InChI key

CTKINSOISVBQLD-GSVOUGTGSA-N

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General description

Enantioselective esterification of (R)-(+)-glycidol with n-butyric acid in organic media using hybrid gel-entrapped lipase on Celite has been reported.

Application

(R)-(+)-Glycidol may be used in the following synthesis:
  • heteroarylpropane-2,3-diols, useful for combinatorial oligomer synthesis
  • enantiomerically pure (2S,3S)- and (2S,3R)-threoninol and -hydroxyphenylalaninol
  • 2-amino-1,4-anhydro-pentitol and 3-amino-1,5-anhydro-4-deoxy-hexitol with the arabino configuration
  • (S)-4-tosyloxymethyl-2-oxazolidinone, required for the synthesis of protected amino alcohol derivatives
  • 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine [(S)-HPMPC]
  • chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 1B - Eye Dam. 1 - Muta. 2 - Repr. 1B - Self-react. C - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

161.6 °F

Flash Point(C)

72 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tetrahedron Letters, 47, 6401-6401 (2006)
A New Route for Protected Amino Alcohols from (R)-Glycidol. Copper (I) Mediated Alkylation of 4-Tosyloxymethyl-2-oxazolidinone.
Iwama S and Katsumura S.
Bulletin of the Chemical Society of Japan, 67(12), 3363-3365 (1994)
Diastereoselective synthesis of ?-hydroxy-?-amino alcohols,(2S, 3S)-and (2S, 3R)-threoninol and-hydroxyphenylalaninol, from (R)-glycidol via the derived 4-hydroxymethyloxazolidinone.
Katsumura S, et al.
Tetrahedron Asymmetry, 5(2), 161-164 (1994)
Synthesis of amino-1, 4-anhydro-d-pentitols and amino-1, 5-anhydro-d-hexitols with the arabino configuration from (R)-glycidol.
Aragones S, et al.
Tetrahedron Asymmetry, 14(13), 1847-1856 (2003)
Effect of imprinting sol-gel immobilized lipase with chiral template substrates in esterification of (R)-(+)-and (S)-(-)-glycidol.
Furukawa S, et al.
Journal of Molecular Catalysis. B, Enzymatic, 17(1), 23-28 (2002)
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