Deoxyadenosine → HCID 53939218, compound

HRID 1736629Notes

Reaction equation

HRID 1736629 reaction equation
[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)C1.[Si]([O:36][CH2:37][C@H:38]1[O:42][C@@H:41]([N:43]2[C:52]3[N:51]=[CH:50][N:49]=[C:47]([NH2:48])[C:46]=3[N:45]=[CH:44]2)[CH2:40][C@@H:39]1[CH:53]=[CH:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH:53]([C@@H:39]1[C@@H:38]([CH2:37][OH:36])[O:42][C@@H:41]([N:43]2[C:52]3[N:51]=[CH:50][N:49]=[C:47]([NH2:48])[C:46]=3[N:45]=[CH:44]2)[CH2:40]1)=[CH:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

3

Reactant 2

HCID 13730DeoxyadenosineHCID 54207106HCID 54207106, compound

Product 1

HCID 53939218HCID 53939218, compoundYield 91%

Procedure

2'-Deoxyadenosine was conveniently transformed into 5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-styryladenosine in 60% yield utilizing the radical reaction described in Example 82 of application Ser. No. 08/040,903. The 5'-O-TBDPS group of the latter compound was deblocked to provide 2',3'-dideoxy-3'-C-styryladenosine in 91% yield, mp 215°-217° C. Anal.: C18H19N5O2.1/4 H2O Calcd.: C% 63.23; H% 5.74; N% 20.48; Found: C% 63.31; H% 5.68; N% 20.69.

Workup

  1. customthe radical reaction

Sources & evidence

ORD record
ord-7c25bc524cac42be9f4ea8868d2cdd79
Source dataset
uspto-grants-1996_07
Patent number
US05541307

Reaction notes

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