82109-98-6

Upstream product

• 75499-90-0 2,5-anhydro-6-O-benzoyl-1,4-dideoxy-D-erythro-hex-3-ulose 
• 75499-82-0 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 
• 75499-83-1 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 
• 98-88-4 benzoyl chloride 
• 75499-87-5 2,5-anhydro-4,6-di-O-benzoyl-1-chloro-1-deoxy-D-glucitol 
• 75499-89-7 2,5-anhydro-4,6-di-O-benzoyl-1-deoxy-D-ribo-hex-3-ulose 
• 75499-88-6 2,5-anhydro-4,6-di-O-benzoyl-1-deoxy-D-glucitol 

Downstream Products

• 82109-99-7 (2S,3S,5S)-5-hydroxymethyl-2-methyltetrahydrofuran-3-ol 

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.