66323-40-8

Upstream product

• 362505-25-7 1-[5-O-Benzoyl-3-azido-2,3-dideoxy-α,β-D-erythro-pentofuranosyl]-thymine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 371164-35-1 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose 
• 362505-23-5 Methyl 5-O-benzoyl-3-azido-2,3-dideoxy-D-ribofuranoside 
• 863396-37-6 methyl 2-deoxy-αβ-D-threo-pentofuranoside 
• 66323-41-9 1-(5′-O-acetyl-3′-azido-2′,3′-dideoxy-α-D-ribofuranosyl)thymine 
• 66323-42-0 1-(5′-O-acetyl-3′-azido-2′,3′-dideoxy-β-D-ribofuranosyl)thymine 
• 114647-74-4 4,5-O-cyclohexylidene-2,3-dideoxy-aldehydo-D-glycero-trans-pent-2-enose 
• 116195-66-5 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-α-thymidine 
• 132585-88-7 2,2-Dimethyl-propionic acid (2S,3S,5R)-3-azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester 
• 132585-91-2 ((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-tert-butyl-dimethyl-silane 
• 135281-02-6 5-O-acetyl-3-azido-1-O-(4-biphenylcarbonyl)-2,3-dideoxy-D-erythro-pentofuranose 
• 122359-33-5 (+)-(2E,4S)-5-Acetoxy-4-(formyloxy)-2-pentenal 
• 135357-51-6 (2E,4S)-5-acetoxy-4-hydroxy-2-pentenal 

Downstream Products

• 1256632-55-9 C₂₃H₃₁N₆O₈P 
• 1352505-13-5 3'-(4-dhlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-α-D-thymidine 

Relevant academic research and scientific papers

Synthesis method of (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound

The invention provides a synthesis method of a (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound, and belongs to the field of organic synthesis. The synthesis method comprises the following steps of dissolving a compound 1 and a chiral phosphoric acid small-molecule catalyst in a solvent to obtain a mixed solution, adding an additive and a halogen source into the mixed solution, and carrying out an olefin asymmetric halogen cyclization reaction to prepare the (1 beta, 2 alpha, 4 beta) halogenated nucleoside compound as shown in a formula I. The synthesis method is simple and convenient in process, suitable for various reaction substrates and wide in application; and the synthesis method has high stereoselectivity on the beta-nucleoside compound and low cost, and the obtained beta-nucleoside compound has the advantages of high yield, high purity and very excellent effect. Meanwhile, the synthesis method is environment-friendly due to no use of a metal catalyst and the like. The synthesis method disclosed by the invention solves the technical problem of preparing the (1 beta, 4 beta) nucleoside compound in the prior art, can be used for efficiently preparing the (1 beta, 4 beta) nucleoside compound, and has a good application prospect.

Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase

We report on Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) inhibitory activities of a series of new 3′- and 5′-modified thymidine analogues including α- and β-derivatives. In addition, several analogues were synthesized in which the 4

Potential application of thymidylate kinase in nucleoside analogue activation in Plasmodium falciparum

Plasmodium falciparum thymidylate kinase (PfTMPK) shows a broad range of substrate tolerance when compared to the corresponding human enzyme. Besides 2′-deoxythymidine monophosphate (dTMP), PfTMPK can phosphorylate 3′-azido-2′,3′-dideoxythymidine monophos

A simple and efficient synthesis of 3prime;-azido-3′-deoxythymidine (AZT) employing a convergent route

The syn-homoallyl alcohol 2a has been prepared with absolute stereoselectivity following PDC oxidation of the mixture of diastereomers 2a, 2b and subsequent K-selectride reduction of the resulting ketone 3. Compound 2a has been efficiently utilized for a simple synthesis of AZT I in a convergent manner.

A novel synthesis of AZT

A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and D-mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step.

Stereoselective synthesis of 3-azido-2,3-dideoxy-D-ribose derivatives and its utilization for the synthesis of anti-HIV nucleosides [1]

Detail account of the synthesis of 3'-azido nucleosides utilizing 3- azido-2,3-dideoxy-D-ribose derivative 7 as the key intermediate was described. The key intermediate 7 was synthesized from D-mannitol in 8 steps in a preparative scale. The Michael reaction of the azide group with α,β- unsaturated-γ-butyrolactone 4 was affected by the steric bulkiness of the substituent at the 5-O position. A bulky t-butyldiphenylsilyl substitution at 5-O gave almost exclusively the α-azido adduct 5b, while unsubstitution at 5-O produced I:1 mixture of α-and β-adducts. The ratio of α to β anomers in the condensation between azido acetate 7a and pyrimidine bases for the preparation of AZT and AZDU was greatly influenced by the solvent and the Lewis acid catalyst used. In the synthesis of 12(AZDU, CS-87), the combination of dichloroethane and trimethylsilyl triflate gave an optimal result, while in the case of 14(AZT), various conditions gave similar ratio of α,β anomers. The azido intermediate 7b was also utilized for the synthesis of several 3'-azido purine-like nucleosides 16-27. The glycosylation was also affected by the Lewis acid catalyst. Boron trifluoride etherate gave the desired N1-glycosylated compounds in which the α-anomer was major, but other catalysts such as trimethylsilyl triflate or stannic chloride produced N2-glycosylated compounds as the major products. The newly synthesized purine-like compounds have been tested against HIV, however, none of them showed any significant activity.

Selective deformylation of an α,β-unsaturated sugar aldehyde in a very short synthesis of 3'-azido-3'-deoxythimidine (AZT) and its stereoisomers

(2E,4S)-5-Acetoxy-4-formyloxy-2-pentenal (2) prepared in one step from tri-O-acetyl-d-glucal was selectively deformylated to give the α,β-unsaturated aldehyde 3 with an unprotected hydroxy group at C-4. Michael-type addition reaction of hydrazoic acid to 3 followed by acylation at C-1 gave a 1:1 mixture of the erythro- and threo-isomers of 5-O-acetyl-3-azido-1-O-(4-biphenylcarbonyl)-2,3-dideoxypentofuranoses 4 and 5. They were used as substrates for nucleoside coupling with silylated thymine to give all four D-isomers of 3'-azido-3'-deoxythymidine 6-9.

Coupling reaction of 1-thiopentofuranosides with silylated pyrimidine bases by activation with N-bromosuccinimide: Synthesis of 3'-Azido-3'-deoxythymidine and its related nucleoside analogs

3'-Azido-3'-deoxythymidine, 3'-fluoro-3'-deoxythymidine, and their 2'-C-substituted derivatives and L-enantiomers were synthesized by the coupling reaction of the corresponding phenyl 1-thiopentofuranosides with silylated thymine by activation with N-bromosuccinimide.

AN EFFICIENT TOTAL SYNTHESIS OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT) AND 3'-AZIDO-2',3'-DIDEOXYURIDINE (AZDDU, CS-87) FROM D-MANNITOL

An efficient stereoselective total synthesis of 3'-azido-3'deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (AZDDU, CS-87) from readily available and inexpensive starting material, D-mannitol has been achieved.