Preparation of the 2'-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation.
The purine nucleoside 2,6-diaminopurine-2'-deoxyriboside is prepared by the direct glycosylation of the 2,6-bis(tetramethylsuccinimide) derivative of the parent purine heterocycle 4 with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride 5 using the sodium salt method. 2'-Deoxyisoguanosine is prepared from 2,6-diaminopurine by a five-step procedure. The purine heterocycle isoguanine is prepared by selective diazotization of 2,6-diaminopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O(2)-carbonyl with TMSCl, the N(6)-amino group is protected as the tetramethylsuccinimide (M(4)SI). The O(2)-carbonyl is protected as the DPC derivative, and the trityl group is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.
Arico
Joseph W
JW
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Calhoun
Amy K
AK
McLaughlin
Larry W
LW
D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000241:Adenosine; D006031:Glycosylation; D006147:Guanine / Q000138:chemical synthesis* / Q000737:chemistry; D006151:Guanosine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D009705:Nucleosides; D011684:Purine Nucleosides; D006151:Guanosine; C008184:isoguanosine; D015075:2-Aminopurine; C007300:2,6-diaminopurine; D006147:Guanine; C008183:isoguanine; D000241:Adenosine