Methanesulfonyl chloride → Vidarabine

HRID 2256196Notes

Reaction equation

HRID 2256196 reaction equation
[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH2:19])[O:7][C@H:6]([CH2:8][OH:9])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(O)(=O)C>[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH2:19])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[S:21]([O:3][C@@H:2]1[C@@H:4]([OH:5])[C@@H:6]([CH2:8][OH:9])[O:7][C@H:1]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][CH:13]=[N:14][C:15]=2[NH2:19])([CH3:20])(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 447916Adenine xyloside

Product 2

HCID 21704VidarabineHCID 22875318HCID 22875318, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-β-D-Arabinofuranosyl adenine (ara-A) is synthesized when the 3',5'-di-O-isopropylidene derivative of 9-(β-D-xylofuranosyl)adenine is treated with methanesulphonyl chloride to convert it to the corresponding 2'-O-mesyl derivative, which is cleaved by acetic acid to produce 9-(2'-O-mesyl-β-D-xylofuranosyl)adenine, which is treated with sodium methoxide in methanol to produce the 2',3'-epoxide, which is treated with sodium in aqueous dimethylformamide to open the ring and produce ara-A which is purified by crystallization.

Sources & evidence

ORD record
ord-b7132e5f9ae4412f959013b77ac05f98
Source dataset
uspto-grants-1997_08
Patent number
US05654286

Reaction notes

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