32077-67-1

Basic information

• Product Name: 3-amino-1-(6-amino-purin-9-yl)-α-L-1,3-dideoxy-ribofuranose
• CAS NO: 32077-67-1
• Molecular Weight: 266.26
• Mol File: 32077-67-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 3-amino-1-(6-amino-purin-9-yl)-α-L-1,3-dideoxy-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-1-(6-amino-purin-9-yl)-α-L-1,3-dideoxy-ribofuranose(32077-67-1)
• EPA Substance Registry System: 3-amino-1-(6-amino-purin-9-yl)-α-L-1,3-dideoxy-ribofuranose(32077-67-1)

Safety Data

• Hazardous Substances Data: 32077-67-1(Hazardous Substances Data)

Upstream product

• 889875-56-3 di-O-benzoyl-3-phthalimido-3-deoxy-β-D-ribofuranosyl chloride 
• 695183-20-1 3'-azido-3'-deoxy-2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 
• 118525-25-0 9-[2',5'-bis-(O-tert-butyldimethylsilyl)-β-D-xylofuranosyl]-9H-adenine 
• 86734-95-4 9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 
• 216976-72-6 Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-71-5 Benzoic acid (3R,4R,5S)-4-azido-2-methoxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-70-4 Carbonic acid (3aR,5S,6R,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester methyl ester 
• 114861-16-4 Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 216976-56-6 ((3aR,5S,6R,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 
• 114861-14-2 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 23345-80-4 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 87-72-9 D-Xylose 

Downstream Products

• 181229-67-4 3-Amino-3-deoxy-L-ribose 
• 223116-03-8 3'-(N-tert-butyloxycarbonyl-L-phenylalanyl-amido)-3'-deoxyadenosine 
• 53-79-2 puromycin 
• 57183-05-8 tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate 
• 58-60-6 3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine 
• 80015-76-5 9-(3-Amino-3-desoxy-β-D-ribofuranosyl)guanin 
• 168985-12-4 Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-(6-amino-purin-9-yl)-4-tert-butoxycarbonylamino-5-(hydroxy-phosphonomethyl-phosphinoyloxymethyl)-tetrahydro-furan-3-yl ester 
• 168985-11-3 C₂₉H₃₄N₆O₉S₂ 
• 168985-13-5 Toluene-4-sulfonic acid (2R,3R,4R,5S)-4-amino-2-(6-amino-purin-9-yl)-5-(hydroxy-phosphonomethyl-phosphinoyloxymethyl)-tetrahydro-furan-3-yl ester 
• 168985-14-6 3'-Amido-3'-desoxy-2'-O-tosyladenosin-3',5'-cyclomethylenbis(phosphonat) 

Relevant articles and documents

Studies on sugar puckering and glycosidic stabilities of 3′-amino-5′-carboxymethyl-3′,5′-dideoxy nucleoside mimics

The synthesis of nucleoside amino acid monomers and dimers has been carried out to evaluate and characterize the impact of the neutral amide backbone on key attributes like puckering of the sugar rings and glycosidic bond strengths of these analogs. The conformational analysis suggests that amide-linked nucleotides have a high predilection towards N-type conformers. The glycosidic bond strength was found to be slightly weaker compared to ribonucleosides under acidic conditions at high temperatures. The results will be helpful to explore in future the development of fully amide-linked oligonucleotides for therapeutic purposes.

A new protecting group '3′,5′-O-sulfinyl' for xylo-nucleosides. A simple and efficient synthesis of 3′-amino-3′-deoxyadenosine (a puromycin intermediate), 2,2′-anhydro-pyrimidine nucleosides and 2′,3′-anhydro-adenosine

We developed a new protecting group, the cyclic sulfite for the protection of the 3′,5′-dihydroxy group of nucleosides. Seven cyclic sulfites, 4a-c, 5a-b, and 6a-b were prepared in high yields from the corresponding xylo-uridines 1 and 2, and xylo-adenosines 3 with thionyl chloride, respectively. Synthesis of the puromycin intermediate 8 was carried out by deprotection of the sulfite moiety through an intramolecular cyclization of the 2′-α-carbamate 7.

Syntheses of puromycin from adenosine and 7-deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair

Protection (05′) of 2′,3′-anhydroadenosine with tert-butyldiphenylsilyl chloride and epoxide opening with dimethylboron bromide gave the 3′-bromo-3′-deoxy xylo isomer which was treated with benzylisocyanate to give the 2′-O-(N-benzylcarbamoyl) derivative. Ring closure gave the oxazolidinone, and successive deprotection concluded an efficient route to 3′-amino-3′-deoxyadenosine. Analogous treatment ofthe antibiotic tubercidin {7-deazaadenosine; 4-amino-7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine} gave 3′-amino-3′-deoxytubercidin. Trifluoroacetylation of the 3′-amino function, elaboration of the heterocyclic amino group into a (1,2,4-triazol-4-yl) ring with N,N′-bis-[(dimethylamino)methylene]hydrazine, and nucleophilic aromatic substitution with dimethylamine gave puromycin aminonucleoside [9-(3-amino-3-deoxy-β-D-ribofuranosyl)-6-(dimethylamino)purine] and its 7-deaza analogue. Aminoacylation [BOC-(4-methoxy-L-phenylalanine)] and deprotection gave puromycin and 7-deazapuromycin. Most reactions gave high yields at or below ambient temperature. Equivalent inhibition of protein biosynthesis in a rabbit reticulocyte system and parallel growth inhibition of several bacteria were observed with the 7-aza/deaza pair. Replacement of N7 in the purine ring of puromycin by "CH" has no apparent effect on biological activity.