75499-82-0

Upstream product

• 69-65-8 mannitol 
• 98-88-4 benzoyl chloride 
• 67-64-1 acetone 
• 65729-81-9 2,5-anhydro-1,3-O-isopropylidene-D-glucitol 
• 27826-73-9 2,5-anhydro-D-glucitol 
• 37699-02-8 (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 198775-13-2 ((3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 

Downstream Products

• 75499-83-1 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 
• 77890-04-1 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol 
• 198775-25-6 ((2R,5S)-5-Trityloxymethyl-2,5-dihydro-furan-2-yl)-methanol 
• 198775-19-8 2,5-anhydro-4,6-di-O-benzoyl-1-O-t-butyldimethylsilyl-D-glucitol 
• 198775-23-4 2,5-anhydro-1-O-t-butyldimethylsilyl-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol 
• 198775-21-2 2,5-anhydro-1-O-t-butyldimethylsilyl-6-O-triphenylmethyl-D-glucitol 
• 198775-36-9 2,5-anhydro-4,6-di-O-benzoyl-1-(N-3-benzoylthymin-1-yl)-3-deoxy-D-ribo-hexitol 
• 198775-27-8 3-Benzoyl-5-methyl-1-((2R,5S)-5-trityloxymethyl-2,5-dihydro-furan-2-ylmethyl)-1H-pyrimidine-2,4-dione 
• 75499-90-0 2,5-anhydro-6-O-benzoyl-1,4-dideoxy-D-erythro-hex-3-ulose 
• 75499-85-3 2,5:3,4-dianhydro-1-O-p-tolylsulphonyl-D-allitol 
• 75499-88-6 2,5-anhydro-4,6-di-O-benzoyl-1-deoxy-D-glucitol 
• 75499-89-7 2,5-anhydro-4,6-di-O-benzoyl-1-deoxy-D-ribo-hex-3-ulose 
• 75499-87-5 2,5-anhydro-4,6-di-O-benzoyl-1-chloro-1-deoxy-D-glucitol 
• 75499-84-2 2,5-anhydro-4,6-di-O-benzoyl-1,3-di-O-p-tolylsulphonyl-D-glucitol 

Relevant academic research and scientific papers

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Ethambutol-sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycoba

Synthesis of homo-C-D4T and homo-C-thymidine

β-C-Vinyl glycoside of D-arabinofuranose was converted to the β-C- hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'- didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.

A Stereospecific Synthesis of (+)-Muscarine

A stereospecific synthesis of (+)-muscarine (1) is described in which acid-catalysed cyclisation of D-mannitol gives 2,5-anhydro-D-glucitol, isolated as its 1,3-O-isopropylidene-4,6-dibenzoate (3); acid hydrolysis then tosylation gives the 1,3-di-O-tosyl derivative (7), converted by sodium methoxide-methanol into 2,5:3,4-dianhydro-1-tosyl-D-allitol (8).This epoxide with sodium bis-(2-methoxyethoxy)aluminium hydride gives 2,5-anhydro-1,4-dideoxy-d-ribo-hexitol (10) and its 1,3-dideoxy-isomer (11) (12:1).The former, with tosyl chloride then trimethylamine gives (+)-muscarine tosylate, also isolated as chloride and bromide salts.