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

• 5451-40-1 2,6 dichloropurine 
• 75788-35-1 9-Trimethylsilyl-2,6-dichlorpurin 
• 1904-98-9 2,6-diaminopurine 
• 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

Scaleable processes for the synthesis of (-)-β-d-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (-)-β-d-2-aminopurine dioxolane (APD)

An efficient and scalable synthesis of (-)-DAPD and (-)-APD has been developed. We discovered that t-butyl cyanoacetate can be used as a new additive for the sugar nucleoside base coupling step en route to DAPD with improved β-selectivity and an isolated yield four-fold greater than the original process scale method. Using this new process, (-)-DAPD has been prepared on greater than 20 g scale. In the synthesis of (-)-APD, a key enzyme-catalyzed hydrolysis reaction afforded the water soluble deprotected α-anomer while leaving the β-anomer completely untouched.

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.