1-β-d-ARABINOFURANOSYL-2′,3′,5′-TRIACETATE

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Names

[ CAS No. ]:
6742-07-0

[ Name ]:
1-β-d-ARABINOFURANOSYL-2′,3′,5′-TRIACETATE

[Synonym ]:
triacetylcytarabine
2',3',5'-tri-O-acetyl-arabinofuranosyl-cytidine
AraC 2',3',5'-tri-O-acetyl ester

Chemical & Physical Properties

[ Density]:
1.52g/cm3

[ Boiling Point ]:
507.4ºC at 760 mmHg

[ Molecular Formula ]:
C15H19N3O8

[ Molecular Weight ]:
369.32700

[ Flash Point ]:
260.6ºC

[ Exact Mass ]:
369.11700

[ PSA ]:
149.04000

[ Index of Refraction ]:
1.61

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA5600000
CHEMICAL NAME :
Cytosine, 1-beta-D-arabino-furanosyl-, 2',3',5'-triacetate
CAS REGISTRY NUMBER :
6742-07-0
LAST UPDATED :
199606
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C15-H19-N3-O8
MOLECULAR WEIGHT :
369.37
WISWESSER LINE NOTATION :
T6NVNJ DZ A- BT5OTJ COV1 DOV1 E1OV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5010 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
680 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg/5D-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
750 mg/kg/15D-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
3 gm/kg/15D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes primarily in glomeruli Blood - thrombocytopenia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
750 mg/kg/15D-I
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Leukocyte
DOSE/DURATION :
49 umol/L
REFERENCE :
CCCCAK Collection of Czechoslovak Chemical Communications. (Academic Press Inc. Ltd., 24-28 Oval Rd., London NW1 7DX, UK) V.1- 1929- Volume(issue)/page/year: 49,2551,1984

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 2(1H)-Pyrimidinone,3,4-dihydro-4-thioxo-1-(2,3,5-tri-O-acetyl-b-D-arabinofuranosyl)-
  • [5-(4-acetamido-2-oxo-pyrimidin-1-yl)-3,4-diacetyloxy-oxolan-2-yl]methyl acetate
  • Cytarabine hydrochloride
  • 4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one
  • 2,2'-Cyclouridine
  • 1-β-D-Arabinofuranosyluracil
  • Uridine
  • 2,4(1H,3H)-Pyrimidinedione,1-(2,3,5-tri-O-acetyl-b-D-arabinofuranosyl)-
  • tri-O-acetyl-N4-(1-(5-nitrothien-2-yl)ethyl)oxycarbonyl-1-β-D-arabinofuranosylcytosine

DownStream

  • Cytarabine

Related Compounds

  • 4-(3-nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-one
  • 2',3',5'-tri-O-acetyl-4-(1,2,4-triazol-1-yl)uridine
  • 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-4-cyano-5-aminoimidazole
  • 3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-4-deoxy-arabinouridine
  • 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-iodocytosine
  • 3-(1-β-D-Arabinofuranosyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl)acrylic acid
  • 2,5-dichloro-N-ethyl-4-methylbenzene-1-sulfonamide
  • N-ethyl-1,3-dihydro-2-benzofuran-5-sulfonamide
  • N-ethyl-5,6,7,8-tetrahydronaphthalene-1-sulfonamide
  • 4-bromo-3-fluoro-N,2-dimethylbenzene-1-sulfonamide
  • 6-methanesulfonyl-N-methylpyridine-3-sulfonamide
  • 2-chloro-6-methyl-N-propylbenzene-1-sulfonamide
  • Ethyl 4-azaspiro[bicyclo[2.2.2]octane-2,3'-pyrrolidine]-4'-carboxylate
  • Ethyl 8-methyl-8-azaspiro[bicyclo[3.2.1]octane-3,3'-pyrrolidine]-4'-carboxylate
  • Ethyl 2,6-diazaspiro[3.4]octane-8-carboxylate
  • Ethyl 1,1-dimethyl-2-oxa-7-azaspiro[4.4]nonane-9-carboxylate
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