42776-78-3

Cordycepin is a purine nucleoside analog with potent and diverse biological activities. Herein, we designed two methods to synthesize cordycepin. One method mainly converted the 3′-OH group into an iodide group and further dehalogenation to yield the final product. Although this method presented a short synthetic procedure, the synthesis had a low overall yield, resulting in only 13.5% overall yield. To improve the overall yield of cordycepin, another synthetic route was studied, which consisted of four individual steps: (1) 5′-OH protection (2) esterification (3) -O-tosyl (-OTs) group removal (4) deprotection. The key step in the synthetic method involved the conversion of 5′-O-triphenylmethyladenosine to 3′-O-tosyl-5′-O-triphenylmethyladenosine, using LiAlH4 as reducing agent. The main advantages of this route were an acceptable total product yield and the commercial availability of all starting materials. The optimal reaction conditions for each step of the route were identified. The overall yield of cordycepin obtained from adenosine as the starting material was 36%.

The invention discloses a synthesis method for 2'-deoxyadenosine monohydrate. Adenosine is esterified and acylated by an acylating agent and an acid-binding agent so that acylate can be obtained, the acylate is subjected to reduction and purification, and then 2'-deoxyadenosine monohydrate is obtained, wherein in the esterifying process, dialkyl group stannic oxide is adopted as an esterifying agent. According to the method, reaction selectivity is high, chromatographic separation is not needed, cost is low, and the yield is high; the synthesis method is applicable to industrial production.

(Chemical Equation Presented) A variant of the semipinacol rearrangement that was observed in our laboratory has been applied to the synthesis of several furanose and pyranose derivatives. The process consists of an "orchestrated" [1,2]-hydride shift with

A new method for deprotecting acetyl groups of blocked purine nucleosides has been established by using tri-n-butyltin hydride (n-Bu3SnH) in the presence of α, α′-azobisisobutyronitrile (AIBN) without affecting OTs group.

A substoichiometric amount (10-20 mol%) of dibutyltin dichloride 1 was found to be effective for promoting the regioselective 2′-O-tosylation of adenosine 2 with TsCl in a one-pot manner, wherein a turnover step for tin dichloride 1 was involved. Dibutylc

The initial step in the mechanism-based inactivation of ribonucleotide reductases by 2'-chloro-2'deoxynucleotides is abstraction of H3' by a proximal free radical on the enzyme. The C3' radical is postulated to undergo spontaneous loss of chloride, and th

The reaction of lithium triethylborohydride with the 2',3'-di-O-p-tolylsulphonyl derivatives of 9-β-D-ribofuranosyladenine, 9-β-D-arabinofuranosyladenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied.The reaction of 2',3'-di-O-p-tolylsulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine.This rearrangement reaction was used for the synthesis of 9-(3,5-dideoxy-β-D-threo-pentofuranosyl)adenine in one step from 2',3',5'-tri-O-p-tolylsulphonyladenosine in 58percent yield.The p-tolylsulphonyl group in the 2'-"up" configuration of unprotected adenine nucleosides was preferentially attacked by LiEt3BH giving S-O-bond scission.This was shown by the formation of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine from 2',3'-di-O-p-tolylsulphonyl-9-β-D-arabinofuranosyladenine and by the formation of 9-β-D-lyxofuranosyladenine from 2'-O-p-tolylsulphonyl-9-β-D-lyxofuranosyladenine with LiEt3BH. 9-β-D-Lyxofuranosyladenine was synthesized from 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenosine in 88percent yield using a triflate displacement reaction.

2'-Azido-2',3'-dideoxyadenosine (9) has been synthesized from adenosine (1) in 6-8 steps.The key intermediate, N6,O5'-bis(4,4'-dimethoxytrityl)-9-(3-deoxy-β-D-threo-pentofuranosyl)adenine (6a), was prepared in a one-flask manner by t

The regioselective mono-O-p-toluenesulfonylation of nucleosides under phase-transfer conditions in which dibutyltin oxide acts as a base is reported.The selectivity is dependent upon both the solvent and ammonium quaternary salt.

Lewis acid catalyzed glycosylation of the 2'-tosyl ribofuranose derivative 5 leads exclusively to β-nucleosides in the uridine and adenosine series.