169287-69-8

Basic information

• Product Name: 2-[2-(benzyloxycarbonyl)amino-6-oxo-1,6-dihydro-9H-purin-9-yl]acetic acid
• Synonyms: 2-[2-(benzyloxycarbonyl)amino-6-oxo-1,6-dihydro-9H-purin-9-yl]acetic acid
• CAS NO: 169287-69-8
• Molecular Weight: 343.299
• Mol File: 169287-69-8.mol
• Article Data: 3

Chemical Properties

• Density: 1.60±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-[2-(benzyloxycarbonyl)amino-6-oxo-1,6-dihydro-9H-purin-9-yl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(benzyloxycarbonyl)amino-6-oxo-1,6-dihydro-9H-purin-9-yl]acetic acid(169287-69-8)
• EPA Substance Registry System: 2-[2-(benzyloxycarbonyl)amino-6-oxo-1,6-dihydro-9H-purin-9-yl]acetic acid(169287-69-8)

Safety Data

• Hazardous Substances Data: 169287-69-8(Hazardous Substances Data)

Usage

Chemical class

Purine derivative

Purine ring

1,6-dihydro-9H-purin-9-yl

Substitution at 2-position

Benzyloxycarbonyl group

Substitution at 6-position

Amino group

Attached group

Carboxylic acid

Potential pharmacological applications

Similarity to purine nucleosides with various biological activities

Protecting group

Benzyloxycarbonyl group for selective deprotection of the amino group

Interest in medicinal chemistry and drug development

Design of novel purine-based compounds with potential therapeutic properties.

Upstream product

• 568585-75-1 [2-(benzyloxycarbonyl)-amino-6-iodopurin-9-yl]-acetic acid 

Downstream Products

• 1352089-43-0 N-[9-(allyloxycarbonyl)-15-{2-[1,6-dihydro-6-oxo-2-(phenylmethoxycarbonylamino)-9H-purin-9-yl]acetyl}-3-(tert-butoxycarbonyl)-20-(morpholin-4-yl)-5,11,17-trioxo-3,6,9,12,15,18-hexaazaicos-1-yl]carbamic acid phenylmethyl ester 
• 1352089-54-3 Boc-Aeg(C[z])-Aeg(Alloc)-Aeg(G[z])-OBn 
• 568586-06-1 4-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(2-nitro-benzenesulfonyl)-piperazin-2-one 
• 620629-20-1 1-(benzothiazole-2-sulfonyl)-4-{[2-N-(benzyloxycarbonyl)-guanin-9-yl]-acetyl}-piperazin-2-one 
• 399565-02-7 {[(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-[2-(2-{[(6-benzyloxycarbonylamino-purin-9-yl)-acetyl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-benzyl]-amino}-acetylamino)-benzyl]-amino}-acetic acid tert-butyl ester 
• 399564-94-4 {(2-amino-benzyl)-[(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 915781-82-7 C₃₁H₃₄N₈O₁₀ 
• 909866-95-1 {(3-benzyloxy-2-tert-butoxycarbonylamino-propyl)-[(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-amino}-acetic acid ethyl ester 
• 399564-87-5 {(2-allyloxycarbonylamino-benzyl)-[(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-amino}-acetic acid tert-butyl ester 
• 169287-77-8 Boc-PNA(G^Z)-OH 
• 193621-94-2 [[2-(2-Benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 1118531-60-4 C₄₇H₅₆N₁₀O₁₂ 

Relevant articles and documents

Development of a convenient route for the preparation of the N 2-Cbz-protected guaninyl synthon required for Boc-mediated PNA synthesis

An efficient, high yielding, chemo- and regioselective, five-step synthetic route to N2-Cbz-guanin-9-yl acetic acid has been developed, which avoids the use of triphosgene. After formation of the N2-Boc protected purine from 2-amino-6-chloropurine, two successive base-controlled alkylations allowed an N9-tert-butyl acetate function followed by an N2-Cbz moiety to be installed. The selectivities of these reactions were confirmed through an X-ray crystallographic study of the 6-(2-nitrophenoxy) analogue. Final hydrolytic dechlorination and removal of the Boc and tert-butyl ester protecting groups were accomplished concomitantly under acidic conditions to afford the guanin-9-yl PNA monomer synthon in an overall yield of 53%.

Fmoc Mediated Synthesis of Peptide Nucleic Acids.

The syntheses of the Fmoc-protected Peptide Nucleic Acid (PNA) monomer pentafluorophenyl esters of adenine (26), cytosine (23), guanine (29) and thymine (20), and their oligomerization are described.The Fmoc PNA backbone 1 is prepared as a stable hydrochl