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857297

Sigma-Aldrich

D-(+)-Ribonic γ-lactone

97%

Synonym(s):

D(+)-Ribono-1,4-lactone

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About This Item

Empirical Formula (Hill Notation):
C5H8O5
CAS Number:
5336-08-3
Molecular Weight:
148.11
Beilstein:
82057
EC Number:
226-256-5
MDL number:
MFCD00063241
UNSPSC Code:
12352202
PubChem Substance ID:
24888436
NACRES:
NA.22

Assay

97%

form

crystals

optical activity

[α]24/D +18°, c = 1 in H2O

mp

85-87 °C (lit.)

SMILES string

OC[C@H]1OC(=O)[C@H](O)[C@@H]1O

InChI

1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1

InChI key

CUOKHACJLGPRHD-BXXZVTAOSA-N

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Application

Important building block for chiral acyclics, cyclopentenones, and oxabicyclic systems. Also employed in studies on nonlinear optical materials.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Aldrichimica Acta, 22, 49-49 (1989)
Chemistry of Materials, 5, 802-802 (1993)
High resolution gas chromatographic/real-time high resolution mass spectrometric identification of organic acids in human urine.
S Lewis et al.
Analytical chemistry, 51(8), 1275-1285 (1979-07-01)
Nucleosides. CXLVIII. Synthesis of 6-(beta-D-ribofuranosyl)picolinamide. A novel C-nucleoside from D-ribonolactone.
M M Kabat et al.
Chemical & pharmaceutical bulletin, 36(2), 634-640 (1988-02-01)
P C Raveendranath et al.
Carbohydrate research, 253, 207-223 (1994-02-03)
A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-protected D-ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi
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