136737-51-4

Basic information

• Product Name: 3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal
• Synonyms: 3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal
• CAS NO: 136737-51-4
• Molecular Weight: 622.871
• Mol File: 136737-51-4.mol

Chemical Properties

• CAS DataBase Reference: 3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal(136737-51-4)
• EPA Substance Registry System: 3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal(136737-51-4)

Safety Data

• Hazardous Substances Data: 136737-51-4(Hazardous Substances Data)

Upstream product

• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 452-51-7 D-2-deoxyribose 
• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 134700-11-1 3,4-di-O-benzyl-2-deoxy-D-erythro-pentose bisbenzyl dithioacetal 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 338742-29-3 1-(3,5-O-dibenzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)-5-nitrouracil 
• 338742-54-4 1-(3,5-O-dibenzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)-5-iodouracil 
• 338742-40-8 9-(3,5-di-O-benzyl-2-deoxy-4-thio-L-threo-pentofuranosyl)adenine 
• 338742-24-8 1-(3,5-di-O-benzyl-2-deoxy-4-thio-L-threo-pentofuranosyl)thymine 
• 338742-53-3 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil 
• 338742-22-6 1-O-acetyl-3,5-di-O-benzyl-2-deoxy-4-thio-α,L-threo-pentofuranose 
• 136737-52-5 benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside 

Relevant articles and documents

Synthesis and structural elucidation of 2′-deoxy-4′-thio-L-threo-pentofuranosylpyrimidine and -purine nucleosides

Benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside (13) was used as glycosyl donor for the synthesis of 4′-thio-L-threo-pentofuranosyluracil derivatives 23-29. The corresponding cytidine analogue 33 was prepared from 13 via the triazolo der

An improved synthesis of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside, an intermediate in the synthesis of 4'-thionucleosides

Treatment of methyl 3,5-di-O-benzyl-2-deoxy-α,β-D-erythro-pentofuranoside with α-toluenethiol and conc. hydrochloric acid gave 3,5-di-O-benzyl-2-deoxy-D-erythro-pentose dibenzyl dithioacetal (21).Mesylation of 21 and ring closure gave benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α,β-L-threo-pentofuranoside.Inversion of configuration at C-4 of 21 was achieved by the Mitsunobu reaction, to produce 4-O-benzoyl-3,5-di-O-benzyl-2-deoxy-L-threo-pentose dibenzyl dithioacetal.Successive debenzoylation, mesylation, and ring closure then gave the title compound.Several new dithioacetal derivatives of 2-deoxy-D-erythro-pentose were prepared in exploratory routes to the described thio sugar or as intermediates.