ChemicalBook CAS DataBase List Vidarabine

Vidarabine synthesis

6synthesis methods

Product Name:Vidarabine
CAS Number:5536-17-4
Molecular formula:C10H13N5O4
Molecular Weight:267.25

Vidarabine, 9-B-arabinofuranosyl-6-amino-9-H-pyrine (36.1.10), is synthesized both microbiologically from the culture fluid of the actinomycete Streptomyces antibioticus NRRL 3238, as well as synthetically. It is synthesized from the acetonide-β-D–xylofuranoside of adenine—9-(3,5-O-isopropyliden-β-D–xylofuranoside)adenine, which is reacted with methanesulfonyl chloride to make the mesylate 9-(3,5-O-isopropyliden-2-O-methansulfonyl-β-D-xydlofuranoside)adenine (36.1.7). Prolonged heating in 90% acetic acid removes the acetonyl protective group from the resulting compound, giving the product (36.1.8).
Reacting this with sodium methoxide leads to the formation of an epoxide— 9-(2,3-anhydro-β-luxofuranosyl)adenine (36.1.9). Finally, heating this epoxide with sodium acetate or benzoate opens the epoxide ring in the dimethylformamide–water system to make the corresponding dihydroxy derivative, vidarabine.

Another way of synthesis of vidarabine that was developed later consists of alkylating of 6-benzamidopurine with 2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride using sodium in liquid ammonia. This simultaneously N-debenzylates the sixth position of the purine system and fulfil O-debenzylation of hydroxyl groups of the furanosyl fragment of the molucule, giving vidarabine.

9H-Purin-6-amine, 9-(2-O-acetyl-β-D-arabinofuranosyl)-

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Yield:5536-17-4 80%

Reaction Conditions:

with ammonia in methanol at 20; for 20 h;

Steps:

1.3
third step,The above solid 10g (0.033mol)Soluble in 100 mL saturated ammonia methanol,Stir the reaction at room temperature for 20hThen the solvent is concentrated to dryness under reduced pressure.Add 100mL hot water, stir, and then activated carbon 0.2g,Warming reflux for 20 minutes,Hot filter activated carbon,The filtrate fell to room temperature and crystallized.The solid was suction filtered and dried to obtain arabidoside 7g. Yield 80%.

References:

Xinxiang Tuoxin Pharmaceutical Co., Ltd.;Xinxiang Pharmaceutical Co., Ltd.;Yang Xining;Li Tao;Liu Pei;Jin Haiyan;Cai Yuying;Wang Xiuqiang CN107556356, 2018, A Location in patent:Paragraph 0019; 0020

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