81739-06-2

Basic information

• Product Name: (2R,3S)-erythro-9-(4-O-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine
• CAS NO: 81739-06-2
• Molecular Weight: 433.488
• Mol File: 81739-06-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S)-erythro-9-(4-O-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-erythro-9-(4-O-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine(81739-06-2)
• EPA Substance Registry System: (2R,3S)-erythro-9-(4-O-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine(81739-06-2)

Safety Data

• Hazardous Substances Data: 81739-06-2(Hazardous Substances Data)

Upstream product

• 81739-04-0 9-(2R,3S)-erythro-(2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine 
• 98-59-9 p-toluenesulfonyl chloride 
• 23918-98-1 eritadenine 
• 81691-56-7 2,3-O-isopropylidene-D-eritadenine ethyl ester 
• 28987-93-1 D-eritadenine ethyl ester 

Relevant articles and documents

Synthesis and Chiroptical Properties of Some Abbreviated NAD+ Analogues

Four novel "abbreviated" NAD+ analogues were prepared by the Zincke reaction.The acyclic chain joining the bases of the analogues bears two stereogenic centers with hydroxyl groups in the both erythro and threo mutual relations.The CD spectra o

STEREOSPECIFIC SYNTHESIS OF ISOMERIC 4-SUBSTITUTED 9-(2,3-DIHYDROXYBUTYL)ADENINES

Reduction of ethyl 2,3-O-isopropylidene-D-tartrate with sodium borohydride afforded (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (Va) which was benzoylated to give monobenzoyl derivative Vd and further transformed into p-toluenesulfonyl derivative Ve.Reaction of the compound Ve with sodium salt of adenine followed by methanolysis gave 2,3-O-isopropylidene derivative Vf which on acid hydrolysis afforded 9-(2S,3S)-(2,3,4-trihydroxybutyl)adenine (Ia).The enantiomer IIa was obtained from 3,4-O-isopropylidene-D-mannitol via (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (VIa) using the same procedure.Reaction of compounds Vf and VIf with p-toluenesulfonyl chloride afforded 4-O-p-toluenesulfonyl derivatives Vg and VIg.These compounds were also obtained from Va and VIa via di-p-toluenesulfonyl derivatives Vc and VIc by reaction with sodium salt of adenine.Treatment of compounds Vg and VIg with sodium iodide gave 4-iodo derivatives Vh and VIh which on reaction with tri-n-butyltin hydride, followed by acid hydrolysis, afforded enantiomeric threo-2,3-dihydroxybutyl derivatives Ib and IIb.Compounds Vg and VIg on treatment with sodium azide, subsequent catalytic hydrogenation of the intermediates Vj and VIj and acid hydrolysis afforded enantiomeric threo-9-(4-amino-2,3-dihydroxybutyl)adenines (Ic, IIc).Reaction of methyl threo-3-phenylglycerate (VIIb) with acetone, followed by reduction with lithium aluminum hydride, gave 2,2-dimethyl-4-phenyl-1,3-dioxolane-5-methanol (VIIIb) which was converted by reaction with p-toluenesulfonyl chloride, condensation with sodium salt of adenine and acid hydrolysis into 9-(RS)-threo-(3-phenyl-2,3-dihydroxypropyl)adenine (I, IId).Methyl ester of D-eritadenine (IXb) was transformed into 2,3-O-isopropylidene derivative XIa which on reduction with sodium borohydride afforded the alcohol XIb.Its acid hydrolysis gave 9-(2R,3S)-erythro-(2,3,4-trihydroxybutyl)adenine (IIIa); tosylation of compound XIb, successive treatment with sodium iodide and tri-n-butyltin hydride and acid hydrolysis afforded 9-(2R,3S)-erythro-(2,3-dihydroxybutyl)adenine (IIIb).The enantiomers IVa and IVb were obtained analogously from L-eritadenine.The racemic derivative Ib + IIb was prepared from (RS)-threo-2,3-dihydroxybutyric acid via p-toluenesulfonyl derivative of racemic 2,2,4-trimethyl-1,3-dioxolane-5-methanol (IIIc) by reaction of sodium salt of adenine followed by acid hydrolysis.