114071-60-2

Upstream product

• 114071-58-8 methyl 3,5-O-isopropylidene-2-O-<(methylthio)-thiocarbonyl>-αβ-D-xylofuranoside 
• 116195-62-1 methyl 2-deoxy-3,5-O-isopropylidene-αβ-D-threo-pentofuranoside 
• 112245-59-7 methyl 3,5-O-isopropylidene-αβ-D-xylofuranoside 
• 1824-96-0 methyl xylofuranoside 
• 532-20-7 D-xylofuranose 
• 130144-86-4 (2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran 
• 863396-37-6 methyl 2-deoxy-αβ-D-threo-pentofuranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 134736-71-3 Methyl 3-O-benzoyl-5-O-tert-butyldiphenylsilyl-2-deoxy-β-D-threo-pentofuranoside 

Downstream Products

• 134736-72-4 Methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-β-D-erythro-pentofuranoside 
• 134736-69-9 Methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-(3-oxopropyl)-β-D-erythro-pentofuranoside 
• 116195-64-3 methyl 5-O-tert-butyldiphenylsilyl-3-cyano-2,3-dideoxy-β-D-erythro-pentafuranoside 
• 116195-63-2 methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-fluoro-β-D-erythro-pentafuranoside 
• 114071-61-3 methyl 5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(trifluoromethanesulfonyl)-β-D-erythro-pentofuranoside 

Relevant academic research and scientific papers

METHYL 5-O-TERT-BUTYLDIPHENYLSILYL-2-DEOXY-D-THREO-PENTOFURANOSIDE; AN APPROACH TO THE SYNTHESIS OF 3'-SUBSTITUTED-2',3'-DIDEOXYNUCLEOSIDES INCLUDING 3'-AZIDO-3'-DEOXYTHYMIDINE AND OF 3'-SUBSTITUTED-2',3'-DIDEOXY-C-NUCLEOSIDES

The Barton deoxygenation of methyl 3,5-O-isopropylidene-αβ-D-xylofuranoside is the key step in a short synthesis of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-αβ-D-threo-pentofuranoside (1) from D-xylose.The syntheses of methyl 2,3-dideoxy-3-fluoro-αβ-D-erythro-pentofuranoside and of a protected 3-azido-2,3-dideoxy-D-erythro-pentofuranose, a possible intermediate for the synthesis of 3'-azido-3'-deoxythymidine (AZT), are reported and the potential of (1) as a divergent intermediate for the preparation of 3'-substituted-2',3'-dideoxynucleosides and C-nucleoside analogues is discussed.

Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives

Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions (tBuOOH, Ti(OiPr)4, Et2iPrN). Th

Synthesis of 1-thymines

Free radicals generated by reaction of protected methyl 2,3-dideoxy-3-iodopentofuranosides 2, 3, and 9 with tributyltin hydride in the presence of a radical initiator (AIBN) were treated with acrolein to give methyl 2,3-dideoxy-3-(3-oxopropyl)pentofuranosides 4 and 5.Reduction of 5 with sodium borohydride followed by protection of hydroxy groups by reaction with tert-butyl chlorodiphenylsilane gave the carbohydrate derivative 11 which was condensed with silylated thymine to afford a separable mixture of α- and β-nucleosides 13 and 14.These nucleosides were subsequently deprotected to give the 3'-propyl-extended thymidine 16 and its corresponding α-isomer 15. Key Words: Thymidine, 3'-deoxy-3'-(3-hydroxypropyl)- / Nucleoside synthesis / Carbohydrates, branched