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Key Documents

49800

Sigma-Aldrich

D-(+)-Glyceraldehyde

≥98.0% (HPLC)

Synonym(s):

(2R)-2,3-Dihydroxypropanal, Triose

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About This Item

Empirical Formula (Hill Notation):
C3H6O3
CAS Number:
Molecular Weight:
90.08
Beilstein:
1720474
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

Assay

≥98.0% (HPLC)

impurities

≤10% water

storage temp.

2-8°C

SMILES string

OC[C@@H](O)C=O

InChI

1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2/t3-/m0/s1

InChI key

MNQZXJOMYWMBOU-VKHMYHEASA-N

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Application

D-(+)-Glyceraldehyde can be utilized as a reactant in the synthesis of:
  • (S)-homophenylalanine by ruthenium oxidation of a 3-amino-1,2-diol generated via coupling of an amine, and α-hydroxyaldehyde.
  • β- and γ-allenols via metal-catalyzed cyclization. Allenols are used as a key precursor for the preparation of enantiopure dihydropyrans and tetrahydrooxepines.
  • Isopropylidene D-glyceraldehyde intermediate, which controls the chirality in the total synthesis of prostaglandins (PGE1).

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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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Highly stereocontrolled one-step synthesis of anti-β-amino alcohols from organoboronic acids, amines, and α-hydroxy aldehydes
Petasis NA and Zavialov IA
Journal of the American Chemical Society, 120(45), 11798-11799 (1998)
Metal-Catalyzed Cyclization of β-and γ-Allenols Derived from d-Glyceraldehyde- Synthesis of Enantiopure Dihydropyrans and Tetrahydrooxepines: An Experimental and Theoretical Study
Alcaide BL
Chemistry?A European Journal , 15(36), 9127-9138 (2009)

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