合成路线:The reaction of adenosine (I) with 2-acetoxyisobutyryl bromide (A) gives the 3'-bromonucleoside (II) along with some 3'-bromo regioisomer (III).The reaction of the desired isomer (II) with HCl in methanol yields the intermediate acetylated 3'-bromonucleoside (V) and finally the 3'-bromo-3'-deoxyadenosine (VI).This compound is then debrominated by hydrogenation with H2 over Pd/C in ethanol/water.
参考文献标题:From adenosine to 3'-deoxyadenosine: Development and scale up
文献作者:Aman,S.; et al.
参考来源:Org Process Res Dev 2000,4(6),601
合成路线:The reaction of adenosine (I) with triethyl orthoacetate (II) by means of Ts-OH in acetonitrile gives the bicyclic dioxolane (III),which is treated with acetyl bromide in dichloroethane to yield the acetylated bromonucleoside (IV).The debromination of (IV) by means of Bu3SnH in toluene affords the acetylated target compound (V),which is finally deprotected with ammonia in methanol.
参考文献标题:A convenient preparation of 3'-deoxyadenosine
文献作者:Norman,D.G.; Reese,C.B.
参考来源:Synthesis 1983,304
合成路线:The enantioselective epoxidation of allyl alcohol (I) with 2-phenylisopropyl hydroperoxide (II) and Ti(iPrO)4 in the presence of D-diisopropyl tartrate gives the chiral epoxide (III),which is esterified with pivaloyl chloride to yield the pivalate (IV).The opening of the epoxide ring of (IV) by means of lithium acetylide (V) and BF3/Et2O affords the alkynyl alcohol (VI),which is cyclized by means of Mo(CO)6 and trimethylamine oxide to provide the chiral dihydrofuran (VII).The oxidation of (VII) with OsO4 and 4-methylmorpholine-N-oxide (NMMO) gives the diol (VIII),which is treated with Ac2O to yield the diacetate (IX).The condensation of (IX) with N6-benzoyl-N6,7-bis(trimethylsilyl)adenine (X) by means of Tms-OTf affords the nucleoside (XI).Finally,this compound is deprotected by means of NaOMe in methanol.
参考文献标题:Asymmetric synthesis of nucleosides via molybdenum-catalyzed alkynol cycloisomerization coupled with stereoselective glycosylations of deoxyfuranose glycals and 3-amidofuranose glycals
文献作者:Gleason,M.M.; McDonald,F.E.
参考来源:J Am Chem Soc 1996,118(28),6648
合成路线:The reaction of adenosine (I) 2-acetoxyisobutyryl bromide (A) in acetonitrile/water gives a mixture of the 3-bromo (II) and 2-bromo nucleosides (III),which is treated with Dowex (OH),Amberlite (OH) or methanolic NaOMe to yield the epoxide (IV).Finally,this compound is reduced with LiEt3BH in THF/DMSO or LiAlH4 in THF to afford a mixture of the 2'-deoxy nucleoside (V) and the target compound that are separated by chromatography.Alternatively,the mixture of the nucleosides (II) and (III) is debrominated by reaction with Bu3SnH and AIBN in refluxing toluene to give the same mixture of (V) and the target compound that is separated as before.
参考文献标题:Nucleic acid related compounds.88.Efficient conversions of ribonucleosides into their 2',3'-anhydro,2'(and 3')-deoxy,2',3'-didehydro-2',3'-dideoxy,and 2',3'-dideoxynucleoside analogues
文献作者:Robins,M.J.; et al.
参考来源:J Org Chem 1995,60(24),7902
合成路线:The reaction of adenosine (I) 2-acetoxyisobutyryl bromide (A) in acetonitrile/water gives a mixture of the 3-bromo (II) and 2-bromo nucleosides (III),which is treated with Dowex (OH),Amberlite (OH) or methanolic NaOMe to yield the epoxide (IV).Finally,this compound is reduced with LiEt3BH in THF/DMSO or LiAlH4 in THF to afford a mixture of the 2'-deoxy nucleoside (V) and the target compound that are separated by chromatography.Alternatively,the mixture of the nucleosides (II) and (III) is debrominated by reaction with Bu3SnH and AIBN in refluxing toluene to give the same mixture of (V) and the target compound that is separated as before.
参考文献标题:A convenient preparation of 3'-deoxyadenosine (cordycepin) and 9-[3'(R)-deuterio-beta-D-2'(R)-pentofuranosyl]-adenine
文献作者:Bazin,H.; Chattopadhyaya,J.
参考来源:Synthesis 1985,1108
合成路线:The reaction of adenosine (I) 2-acetoxyisobutyryl bromide (A) in acetonitrile/water gives a mixture of the 3-bromo (II) and 2-bromo nucleosides (III),which is treated with Dowex (OH),Amberlite (OH) or methanolic NaOMe to yield the epoxide (IV).Finally,this compound is reduced with LiEt3BH in THF/DMSO or LiAlH4 in THF to afford a mixture of the 2'-deoxy nucleoside (V) and the target compound that are separated by chromatography.Alternatively,the mixture of the nucleosides (II) and (III) is debrominated by reaction with Bu3SnH and AIBN in refluxing toluene to give the same mixture of (V) and the target compound that is separated as before.
参考文献标题:Regiospecific and stereoselective conversion of ribonucleosides to 3'-deoxynucleosides.A high yield three-stage synthesis of cordycepin from adenosine
文献作者:Hansske,F.; Robins,M.J.
参考来源:Tetrahedron Lett 1985,26(36),4295
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