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2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride structure
CAS No.
10212-25-6
Chemical Name:
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
Synonyms
Cyclo-C;nsc-145668;Cyclo-Cr·HCl;Anhydro-Cr.HCl;NSC 145668 HCl;ANCITABINE HCL;Cyclocytidine HC1;CYCLOCYTIDINE HCL;2,2'-Anhydro-C.Hcl;OCTD hydrochloride
CBNumber:
CB5292165
Molecular Formula:
C9H12ClN3O4
Formula Weight:
261.66
MOL File:
10212-25-6.mol

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Properties

Melting point:
269-270 °C (dec.)(lit.)
alpha 
-21.8 º (c=2,water)
refractive index 
-21 ° (C=2, H2O)
storage temp. 
Inert atmosphere,2-8°C
form 
Powder
color 
White
Merck 
14,629
InChIKey
KZOWNALBTMILAP-JBMRGDGGSA-N
FDA UNII
3T6920M469
NCI Drug Dictionary
ancitabine hydrochloride
SAFETY
  • Risk and Safety Statements
Safety Statements  24/25
WGK Germany  2
RTECS  LV2615000
HS Code  29213000

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A8598 Ancitabine hydrochloride 10212-25-6 1g $90.3 2021-03-22 Buy
TCI Chemical C2207 2,2'-O-Cyclocytidine Hydrochloride >98.0%(HPLC)(N) 10212-25-6 1g $46 2021-03-22 Buy
TCI Chemical C2207 2,2'-O-Cyclocytidine Hydrochloride >98.0%(HPLC)(N) 10212-25-6 5g $134 2021-03-22 Buy
Alfa Aesar J63845 Cyclocytidine hydrochloride, 98+% 10212-25-6 5g $180 2021-03-22 Buy
Alfa Aesar J63845 Cyclocytidine hydrochloride, 98+% 10212-25-6 1g $50.4 2021-03-22 Buy

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Chemical Properties,Uses,Production

Chemical Properties

white fine crystalline powder

Originator

Cyclo-C,Kohjin,Japan,1975

Uses

antineoplastic

Definition

ChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of ancitabine and hydrogen chloride.

Manufacturing Process

A series of reaction steps may be employed in which: (1) Uridine is reacted with trityl chloride to give 5'-o-trityluridine; (2) Imidazole is reacted with thiophosgene and that product reacted with the 5'-o-trityluridine to give 2,2'- anhydro-1-(5'-o-trityl-β-D-arabinofuranosyl)uracil; (3) The preceding uracil product is converted to the thiouracil using hydrogen sulfide; (4) The trityl group is removed by treatment with 80% acetic acid; (5) A triacetylated product is obtained using acetic anhydride; (6) A dithiouracil is prepared from the uracil intermediate using phosphate pentasulfide.
Preparation of 1-(β-D-arabinofuranosyl)-2-thiocytosine: A solution of 2.0 g of 1-(2',3',5'-O-triacetyl-β-D-arabinofuranosyl)-2,4-dithiouracilin 100 ml of methanol is saturated with anhydrous ammonia at 0°C. The mixture, in a glass liner, is heated in a pressure bomb at 100°C for three hours. The reaction mixture is concentrated to a gum in vacuum, and most of the byproduct acetamide is removed by sublimation at 60°C/0.1 mm. The residue is chromatographed on 100 g of silica gel. Elution of the column with methylene chloride-methanol mixtures with methanol concentrations of 2-25% gives fractions containing acetamide and a series of brown gums. The desired product is eluted with 30% methanol-methylene chloride to give a total yield of 0.386 g (30%), MP 175-180°C (dec.). Recrystallization from methanolisopropanol furnishes an analytical sample, MP 180-182°C (dec.).
To a solution of 80 mg of 1-(β-D-arabinofuranosyl)-2-thiocytosine in 12 ml of water is added dropwise 3 ml of a 1 M bromine solution in carbon tetrachloride. At this point the color of the bromine persists for about 2-3 minutes after each addition. The unreacted bromine is blown off with a stream of nitrogen, and the reaction mixture is concentrated to a syrup in vacuum using a bath temperature less than 50°C. The residue is evaporated three times with 10 ml portions of ethanol, whereupon it crystallizes. The product is triturated with cold ethanol and with ether to obtain 17 mg of 2,2'-anhydro-1- (β-D-arabinofuranosyl)cytosine hydrobromide, MP 240°C (dec.).
Treatment of the hydrobromide with a slight excess of ethanolic ammonia yields the base which may then be converted to the hydrochloride.

Therapeutic Function

Antineoplastic

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products


2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Suppliers

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Henan DaKen Chemical CO.,LTD.
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View Lastest Price from 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-22 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
10212-25-6
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-09-29 Cyclocytidine hydrochloride
10212-25-6
US $0.00-0.00 / Kg/Drum 1KG 98%min 500kg WUHAN FORTUNA CHEMICAL CO., LTD
2021-07-13 Cyclocytidine hydrochloride
10212-25-6
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Spectrum


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