2273-78-1

Basic information

• Product Name: 3-isoadenosine
• Synonyms: 3-isoadenosine;3-(β-D-Ribofuranosyl)-3H-purin-6-amine;3-β-D-Ribofuranosyl-3H-purine-6-amine;3H-Purin-6-aMine, 3-b-D-ribofuranosyl-
• CAS NO: 2273-78-1
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.25
• Mol File: 2273-78-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 529.4°C at 760 mmHg
• Flash Point: 274°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 2.04E-13mmHg at 25°C
• Refractive Index: 1.907
• PKA: 12.84±0.70(Predicted)
• CAS DataBase Reference: 3-isoadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-isoadenosine(2273-78-1)
• EPA Substance Registry System: 3-isoadenosine(2273-78-1)

Safety Data

• Hazardous Substances Data: 2273-78-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13N5O4/c11-8-5-9(13-2-12-5)15(3-14-8)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1,11H2/t4-,6-,7-,10-/m1/s1

Upstream product

• 41028-66-4 1,5-anhydroribitol 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 66224-66-6 adenine 

Downstream Products

• 181262-56-6 allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine 
• 181262-54-4 allyl 3'-[N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite 
• 181262-51-1 (3-{(2R,4S,5R)-4-(Allyloxy-diisopropylamino-phosphanyloxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-3H-purin-6-yl)-carbamic acid allyl ester 
• 181262-45-3 {3-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3H-purin-6-yl}-carbamic acid allyl ester 
• 181262-48-6 (3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-3H-purin-6-yl)-carbamic acid allyl ester 
• 181262-42-0 3-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3H-purin-6-ylamine 
• 181262-34-0 Thiocarbonic acid O-[(2R,3R,3aR,9aR)-2-(6-amino-purin-3-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-phenyl ester 
• 172842-00-1 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosine 
• 19046-84-5 2'-deoxy-3-isoadenosine 

Relevant articles and documents

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.