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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:
453-17-8
Molecular Weight:
90.08
Beilstein/REAXYS Number:
1720474
EC Number:
207-217-1
MDL number:
MFCD00064378
UNSPSC Code:
12352200
PubChem Substance ID:
57651224
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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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)
Chiral synthesis of prostaglandins (PGE1) from D-glyceraldehyde
Stork G and Takahashi T
Journal of the American Chemical Society, 99(4), 1275-1276 (1977)
Takayoshi Wakagi et al.
PloS one, 11(1), e0147333-e0147333 (2016-01-26)
Archaea use glycolytic pathways distinct from those found in bacteria and eukaryotes, where unique enzymes catalyze each reaction step. In this study, we isolated three isozymes of glyceraldehyde oxidoreductase (GAOR1, GAOR2 and GAOR3) from the thermoacidophilic archaeon Sulfolobus tokodaii. GAOR1-3
Katarzyna Lechowicz et al.
International journal of molecular sciences, 21(16) (2020-08-13)
Lolium multiflorum/Festuca arundinacea introgression forms have been proved several times to be good models to identify key components of grass metabolism involved in the mechanisms of tolerance to water deficit. Here, for the first time, a relationship between photosynthetic and
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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