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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/REAXYS Number:
82057
EC Number:
226-256-5
MDL number:
MFCD00063241
UNSPSC Code:
12352202
PubChem Substance ID:
24888436
NACRES:
NA.22

Quality Level

200

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Chemistry of Materials, 5, 802-802 (1993)
Aldrichimica Acta, 22, 49-49 (1989)
Tae Woo Kim et al.
Organic letters, 6(22), 3949-3952 (2004-10-22)
[structure: see text] We describe a series of nonpolar nucleoside analogues having similar shapes and gradually increasing size. The structure of the nucleobase thymine was mimicked with toluene derivatives, replacing O2/O4 with hydrogen, fluorine, chlorine, bromine, and iodine. Glycosidic bonds
Cheng-Hung Jen et al.
Nucleosides, nucleotides & nucleic acids, 29(7), 523-534 (2010-07-01)
A thorough study for the synthesis of 1-deazauridine is described. 3-Bromo-2,6-dimethoxy-5-(beta-D-ribofuranosyl)pyridine, a synthetic precursor for 1-deazauridine, was prepared in seven steps from 2,6-dimethoxypyridine and d-ribose via the ribonolactone approach. Subsequent demethylation was unsuccessful but led to presumable anomerization and isomerization.
B A Horenstein et al.
Biochemistry, 32(28), 7089-7097 (1993-07-20)
A new approach to understanding transition-state structure is presented which involves the sequential application of experimental and computational methods. A family of experimentally determined kinetic isotope effects is fit simultaneously in a vibrational analysis to provide a geometric model of
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