N-Hydroxyphthalimide → HCID 54550453, compound

HRID 1736630Notes

Reaction equation

[CH:1]([C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[CH2:10]1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O[N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37]>>[C:31]1(=[O:32])[N:27]([O:15][CH2:14][C@H:13]2[O:12][C@@H:11]([N:16]3[C:25]4[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=4[N:18]=[CH:17]3)[CH2:10][C@@H:9]2[CH:1]=[CH:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:28](=[O:37])[C:29]2=[CH:36][CH:35]=[CH:34][CH:33]=[C:30]12

Participants

Reactant 2

HCID 10665N-Hydroxyphthalimide

HCID 53939218HCID 53939218, compound

Product 1

HCID 54550453HCID 54550453, compoundYield 76%

Procedure

2',3'-Dideoxy-3'-C-styryladenosine underwent standard Mitsunobu reaction with N-hydroxyphthalimide to provide 2',3'-dideoxy-5'-O-phthalimido-3'-C-styryladenosine in 76% yield with a melting point of 145°-147° C. Anal.: C26H22N6O4.1/4 H2O Calcd.: C% 64.12; H% 4.65; N% 17.25; Found: C% 63.96; H% 4.58; N% 17.51.

Sources & evidence

ORD record: ord-193b877edbdc4cc7bb7772ff46018664
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541307

Reaction notes

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