145514-04-1

Basic information

• Product Name: 2,6-diaminopurine dioxolane
• Synonyms: Aids005431;Aids-005431;Dapd;2,6-diaminopurine dioxolane;(2R,4R)-4-(2,6-DIAMINO-9H-PURIN-9-YL)-1,3-DIOXOLAN-2-YLMETHANOL;(-)-(2R,4R)-2-Amino-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]adenine;(-)-.beta.-D-2,6-Diaminopurine dioxolane
• CAS NO: 145514-04-1
• Molecular Formula: C9H12 N6 O3
• Molecular Weight: 252.23
• Mol File: 145514-04-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 676.8°Cat760mmHg
• Flash Point: 363.1°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 3.05E-19mmHg at 25°C
• Refractive Index: 1.917
• CAS DataBase Reference: 2,6-diaminopurine dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-diaminopurine dioxolane(145514-04-1)
• EPA Substance Registry System: 2,6-diaminopurine dioxolane(145514-04-1)

Safety Data

• Hazardous Substances Data: 145514-04-1(Hazardous Substances Data)

Usage

Uses

2,6-diaminopurine dioxolane can be used in the treatment of HIV-1 and hepatitis B infections (reverse transcriptase inhibitor).

InChI:InChI=1/C9H12N6O3/c10-7-6-8(14-9(11)13-7)15(3-12-6)4-2-17-5(1-16)18-4/h3-5,16H,1-2H2,(H4,10,11,13,14)/t4-,5-/m1/s1

Upstream product

• 1904-98-9 2,6-diaminopurine 
• 5451-40-1 2,6 dichloropurine 
• 75788-35-1 9-Trimethylsilyl-2,6-dichlorpurin 
• 108436-98-2 C₁₄H₃₀N₆Si₃ 
• 1904-98-9 2,6-diaminopurine 
• 145513-99-1 (-)-β-D-2-amino-6-chloropurine dioxolane 
• 145440-02-4 (-)-(2R,4R)-2-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-dioxolan-4-yl>-6-chloropurine 
• 855520-14-8 4-methoxybenzoic acid 4(R)-(2,6-dichloro-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester 
• 855520-10-4 isobutyric acid 4(R)-(2,6-dichloro-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester 
• 855520-15-9 4-methoxybenzoic acid 4(R)-(2,6-diamino-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester 
• 838845-03-7 isobutyric acid 4(R)-(2,6-diamino-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester 
• 145440-11-5 9-[(2R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl]-9H-purine-2,6-diamine 

Downstream Products

• 1239439-31-6 (2S)-ethyl 2-(((((2R,4R)-4-(2-amino-6-hydroxy-9H-purin-9-yl)-1,3-dioxolan-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 

Relevant articles and documents

MONOPHOSPHATE PRODRUGS OF DAPD AND ANALOGS THEREOF

The present invention is directed to compounds, compositions and methods for treating or preventing cancer and viral infections, in particular, HIV and HBV, in human patients or other animal hosts. The compounds are certain 6-substituted-2-amino-purine di

Methods to manufacture 1,3-dioxolane nucleosides

This application provides a process for preparing enantiomerically pure β-D-dioxolane nucleosides. In particular, a new synthesis of (?)-DAPD, suitable for large scale development, is described. In one embodiment the invention provides a process for prepa

Stereoselective synthesis of nucleoside analogues

The invention is a process for stereoselectively producing a dioxolane nucleoside analogue from an anomeric mixture of β and α anomers represented by the following formula A or formula B: wherein R is selected from the group consisting of C1-6alkyl and C6-15aryl and Bz is benzoyl. The process comprises hydrolyzing said mixture with an enzyme selected from the group consisting of Protease N, Alcalase, Savinase, ChiroCLEC-BL, PS-30, and ChiroCLEC-PC to stereoselectively hydrolyze predominantly one anomer to form a product wherein R1is replaced with H. The process also includes the step of separating the product from unhydrolyzed starting material. Additionally, the functional group at the C4 position is stereoselectively replaced with a purinyl or pyrimidinyl or derivative thereof.