190430-41-2

Basic information

• Product Name: 2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine
• CAS NO: 190430-41-2
• Molecular Weight: 545.595
• Mol File: 190430-41-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine(190430-41-2)
• EPA Substance Registry System: 2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine(190430-41-2)

Safety Data

• Hazardous Substances Data: 190430-41-2(Hazardous Substances Data)

Upstream product

• 183274-50-2 3-bromo-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 183274-49-9 4-Isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine 
• 100644-65-3 4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine 
• 183274-51-3 6-amino-3-iodo-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine 
• 190430-40-1 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine 

Downstream Products

• 455886-19-8 2-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-N⁴,N⁶,N⁶-triisobutyryl-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 

Relevant articles and documents

Synthesis of 7-halogenated 8-aza-7-deaza-2'-deoxyguanosines and related pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides

The synthesis of 7-bromo and 7-iodo derivatives of 8-aza-7-deaza-2'- deoxyguanosine (2, 3) as well as the halogenated 4-alkoxy derivatives 4a-c and 5a-c is described. Glycosylation of the halogenated pyrazolo[3,4- d]pyrimidine anions of 7a-c or 8a-c with 2-deoxy-3,5-di-O-(p-toluoy)-α-D- erythro-pentofuranosyl chloride (9) yields regioisomeric glycosylation products, the N(1)-isomers 10a-c and 11a-c as well sa the N(2)-compounds 12a- c. The latter isomers lose their halogen during the glycosylation in the presence of non-anhydrous KOH. Anhydrous conditions (NaH) furnished 10c, 11c together with the halogenated N(2)-isomers 13a,b. Compounds 10a-c, and 11a-c were deprotected and converted to the 4-alkoxy nucleosides 4a-c and 5a-c. The N(1)-nucleosides 4c and 5c were hydrolyzed to give the 7-bromo or 7-iodo derivatives of 8-aza-7-deaza-2'-deoxyguanosines 2 and 3. Different from regular 2'-deoxyribonucleosides the sugar moiety of pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides shows a preferred N-type pucker (3T2) in solution, a conformation which is also detected in the solid state.