75499-84-2

Upstream product

• 75499-83-1 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 
• 98-59-9 p-toluenesulfonyl chloride 
• 98-88-4 benzoyl chloride 
• 75499-82-0 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 

Downstream Products

• 75499-85-3 2,5:3,4-dianhydro-1-O-p-tolylsulphonyl-D-allitol 
• 75499-91-1 2,5-anhydro-1,4-dideoxy-6-O-(p-tolylsulphonyl)-D-ribo-hexitol 
• 82083-43-0 (+)-muscarine toluene-p-sulfonate salt 
• 82064-10-6 2,5-anhydro-1,3-dideoxy-6-O-p-tolylsulphonyl-D-ribo-hexitol 

Relevant academic research and scientific papers

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.