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

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

Used in Pharmaceutical Industry:
2,6-Diaminopurine dioxolane is used as an antiviral agent for the treatment of HIV-1 and hepatitis B infections. It functions as a reverse transcriptase inhibitor, which means it interferes with the replication process of these viruses by blocking the activity of the reverse transcriptase enzyme. This inhibition helps to prevent the spread of the virus in the body and can be an essential part of the treatment regimen for patients with these viral infections.

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

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

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.

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

Synthesis of (-)-DAPD

A new synthesis of (-)-DAPD, suitable for large scale development, is described.

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.

2-Substituted-4-substituted-1,3-dioxolanes and use thereof

Nucleoside analogues containing a 1,3-dioxolane structure are suitable antiviral agents, particulary for the treatment of the HIV infections in mammals, especially humans. Examples of the nucleoside analogues include: cis-2-acetoxymethyl-4-(thymin-1′-yl)-1,3,-dioxolane, cis-2-hydroxymethyl-4-(thymin-1′-yl)-1,3-dioxolane, cis-2-benzoyloxymethyl-4-(cytosin-1′-yl)-1,3-dioxolane, and cis-2-hydroxymethyl-4-(cytosin-1′-yl)-1,3-dioxolane. These compounds can be in the form of their racemates or their separate enantiomers.

Enantiomerically pure β-D-dioxolane-nucleosides

A method and composition for the treatment of humans infected with HIV that includes the administration of an HIV treatment amount of an enantiomerically pure β-D-dioxolanyl purine nucleoside of the formula: STR1 wherein R is OH, Cl, NH2, or H,

Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity

A method and composition for the treatment of humans infected with HBV that includes the administration of an HBV treatment amount of a β-dioxolanyl purine nucleoside of the formula: STR1 wherein R is OH, Cl, NH2, or H, or a pharmaceutically acceptable salt or derivative of the compound, optionally in a pharmaceutically acceptable carrier or diluent.

L-β-(2S,4S)- and L-α-(2S,4R)-dioxolanyl nucleosides as potential anti- HIV agents: Asymmetric synthesis and structure-activity relationships

In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and - purine nucleosides have been synthesize

1,3-Dioxolanylpurine nucleosides (2R,4R) and (2R,4S) with selective anti- HIV-1 activity in human lymphocytes

In order to study the structure-activity relationships of dioxolane nucleosides as potential anti-HIV-1 agents, various enantiomers of pure dioxolanylpurine nucleosides were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear cel