142217-81-0

Basic information

• Product Name: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one
• Synonyms: 3',5'-Di-O-benzyl Entecavir;2-AMino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxyMethyl)-2-Methylenecyclopentyl]-6H-purin-6-one (interMediate 7);2-AMino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxyMethyl)-2-Methylenecyclopentyl]-6H-purin;2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)-methyl)-2-methylenecyclopentyl)-1H-purin-6(9H);6H-Purin-6-one,2-amino-1,9-dihydro-9[(1S,3R,4S)-2-methylene-4-(phenylmethoxy)-3-[([phenylmethoxy)methyl]cyclopentyl]-;N-1 Entecavir API;2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-p;Entecavir dibenzylated
• CAS NO: 142217-81-0
• Molecular Formula: C₂₆H₂₇N₅O₃
• Molecular Weight: 457.52
• EINECS: 1312995-182-4
• Mol File: 142217-81-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.34
• Refractive Index: 1.679
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly)
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one(142217-81-0)
• EPA Substance Registry System: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one(142217-81-0)

Safety Data

• Hazardous Substances Data: 142217-81-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 142217-81-0 differently. You can refer to the following data:
1. 3’5’Di-O-benzyl Entecavir is an intermediate in the preparation of the hepatitis B antiviral agent, Entecavir (E558900).
2. 3’,5’-Di-O-benzyl Entecavir is an intermediate in the preparation of the hepatitis B antiviral agent, Entecavir (E558900).

InChI:InChI=1/C26H27N5O3/c1-17-20(15-33-13-18-8-4-2-5-9-18)22(34-14-19-10-6-3-7-11-19)12-21(17)31-16-28-23-24(31)29-26(27)30-25(23)32/h2-11,16,20-22H,1,12-15H2,(H3,27,29,30,32)/t20-,21-,22-/m0/s1

Upstream product

• 142217-77-4 [1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol 
• 1351691-90-1 C₁₇H₁₉N₅O₃ 
• 122-51-0 orthoformic acid triethyl ester 
• 184376-29-2 (S)-3-(benzyloxy)pent-4-en-1-ol 
• 139884-80-3 1,3-O-benzylidene-1,3-dihydroxy-4(Z)-pentane 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 
• 100-52-7 benzaldehyde 
• 1354715-02-8 (1R,3R,4S)-4-benzyloxy-3-(benzyloxymethyl)-2-methylene-cyclopentanol 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 

Downstream Products

• 142217-69-4 entecavir 

Relevant articles and documents

Improved entecavir intermediate synthesis process and improved entecavir synthesis process

The invention discloses an improved entecavir intermediate synthesis process and an improved entecavir synthesis process, and relates to the technical field of drug synthesis. The invention disclosesan improved entecavir intermediate synthesis process. In the synthesis process of an amino protection reaction product, amino protecting groups are added in batches; and the ratio of the reaction rawmaterials is optimized, so that the problems of long reaction time and relatively low amino protection reaction yield due to adoption of a one-time complete feeding mode in an existing synthesis modeare solved, the synthesis time of an amino protection reaction product is shortened to 50-70 minutes, and the obtained product is high in yield and purity. According to the improved entecavir synthesis process, in the amino protection reaction product synthesis process, reaction conditions are effectively optimized, and the purity of obtained entecavir reaches 99% or above.

A New Route for the Synthesis of Entecavir

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BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro

BMS-200475, a never carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED50 = 3 nM) with relatively low cytotoxicity (CC50 = 21-120 μM). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and > 99% optical purity. The enantiomer of BMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active.