857297
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:
Molecular Weight:
148.11
Beilstein:
82057
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.22
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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
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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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