Acetic Anhydride → HCID 54086996, compound

HRID 2071867Notes

Reaction equation

HRID 2071867 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(OC(=O)CC)(=O)CC.C([O:20][C@H:21]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([CH2:30][O:31][Si](C(C)(C)C)(C)C)[O:23][C@H:22]1[N:39]1[CH:47]=[N:46][C:45]2[C:40]1=[N:41][CH:42]=[N:43][C:44]=2[NH2:48])(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.N1C=CC=CC=1>[C:27]([O:26][C@@H:25]1[C@@H:24]([CH2:30][O:31][C:1](=[O:3])[CH3:2])[O:23][C@@H:22]([N:39]2[CH:47]=[N:46][C:45]3[C:40]2=[N:41][CH:42]=[N:43][C:44]=3[NH2:48])[C@H:21]1[OH:20])(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 31263Propionic anhydrideHCID 2724141Tetrabutylammonium FluorideHCID 53723119HCID 53723119, compound

Product 1

HCID 54086996HCID 54086996, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

By substituting 9.5 ml. of acetic anhydride for the propionic anhydride in paragraph 1 (a) and using 200 ml. of dry pyridine, the product obtained by the procedure of paragraph 1 a) is 9-(2,3-di-O-acetyl-5O-(tert-butyldimethylsily)-β-D-arabinofuranosyl)adenine, which, on reaction with 31.3 g. of tetrabutylammonium fluoride in 300 ml. of tetrahydrofuran, following the procedure of paragraph 1 (b), gives 9-(3,5-di-O-acetyl-β-D-arabinofuranosyl)adenine. By substituting 23.4 ml. of butyryl chloride for the propionic anhydride in paragraph 1 (a) and using 17.9 g. of the silyl ether in 250 ml. of pyridine, the product obtained is 9-(2,3-di-O-butyryl-5-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl) adenine, which on reaction with 37 g. of tetrabutylammonium fluoride in 350 ml. of tetrahydrofuran following the procedure of paragraph 1 (b) gives 9-(3,5-di-O-butyryl-β-D-arabinofuranosyl)adenine.

Workup

  1. customon reaction with 31.3 g

Sources & evidence

ORD record
ord-ab8de9e18d194cffb61b04ceeda337a3
Source dataset
uspto-grants-1977_09
Patent number
US04048432

Reaction notes

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