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I5127

Sigma-Aldrich

2′,3′-O-Isopropylideneuridine

≥99% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C12H16N2O6
CAS Number:
362-43-6
Molecular Weight:
284.27
EC Number:
206-647-7
MDL number:
MFCD00034509
UNSPSC Code:
41106305
PubChem Substance ID:
24895983
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to light yellow

storage temp.

−20°C

SMILES string

CC1(C)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O1)N3C=CC(=O)NC3=O

InChI

1S/C12H16N2O6/c1-12(2)19-8-6(5-15)18-10(9(8)20-12)14-4-3-7(16)13-11(14)17/h3-4,6,8-10,15H,5H2,1-2H3,(H,13,16,17)/t6-,8-,9-,10-/m1/s1

InChI key

GFDUSNQQMOENLR-PEBGCTIMSA-N

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Application

2′,3′-O-Isopropylideneuridine is used in the chemical synthesis of N-benzoylated uridine derivatives and N3-substituted 2′,3′-O-isopropylideneuridines with central nervous system (CNS) depressant activity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Anita R Maguire et al.
Carbohydrate research, 337(4), 369-372 (2002-02-14)
An improved procedure for the synthesis of N-benzoyl-2',3'-O-isopropylidene uridine via one-step selective N-benzoylation of 2',3' -O-isopropylidene uridine has been developed. An efficient synthetic route to N-benzoyl thymidine via initial tribenzoylation, followed by selective hydrolysis of the benzoates is also described.
S I Malekin et al.
Bioorganicheskaia khimiia, 23(8), 648-654 (1997-08-01)
New nucleoside-phospholipid conjugates were synthesized based on 1,2-disubstituted glycerides and nucleosides. These contain rac-1-hexadecyl-2-palmitoyl(or 2-methylcarbamoyl)-sn-glycero-3-phosphate as the phospholipid component and 2',3'-didehydro-3'-deoxythymidine, 1-(Z-5-hydroxypentene-2-yl)thymine, or 2',3'-isopropylideneuridine as a nucleoside component. The conjugates were synthesized by three different ways: from rac-1-hexadecyl-2-acyl-sn-glycero-3-phospodichlorides, -3-phosphatidic acids
M L Scholes et al.
International journal of radiation biology, 61(4), 443-449 (1992-04-01)
The effect of pH on base release in the gamma-radiolysis of N2O-saturated solutions of a number of nucleosides (including uridine, 3-methyluridine, 2',3'-O-isopropylidene-uridine, and adenosine) has been investigated. For all these nucleotides, independent of the base or sugar moiety, base release
C S Yao et al.
Chemical & pharmaceutical bulletin, 47(12), 1802-1804 (2000-04-05)
N3-Substituted derivatives of 2',3'-O-isopropylideneuridine (1) were synthesized and their pharmacological effects on the central nervous system (CNS) examined using mice. Methyl (2), ethyl (3), propyl (4), butyl (5), allyl (6), benzyl (7), o-, m-, p-xylyls (8, 9, 10), and alpha-phenylethyl
Tomomi Shimizu et al.
Chemical & pharmaceutical bulletin, 53(3), 313-318 (2005-03-04)
Seventy eight N(3)-substituted derivatives of uridine (1), thymidine (2), 2'-deoxyuridine (3), 6-azauridine (4), 2',3'-O-isopropylideneuridine (5), and arabinofuranosyluracil (6) were synthesized and their antinociceptive effects were evaluated. N(3)-(2',4'-Dimethoxyphenacyl)uridine (1l), N(3)-(2',4'-dimethoxyphenacyl)2'-deoxyuridine (3l), and N(3)-(2',5'-dimethoxyphenacyl)arabinofuranosyluracil (6m) possessed 93, 86, and 82% of the
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