75499-91-1

Upstream product

• 115352-39-1 (2R)-1-benzyloxy-2-hydroxy-pent-4-yne 
• 20031-16-7 L-Rhamnono-1,4-lactone 
• 75499-83-1 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 
• 75499-82-0 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 
• 124251-97-4 (S)-2-(2-Benzyloxy-ethoxy)-propionic acid 
• 75499-86-4 (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 82165-72-8 2,5-anhydro-1,3-dideoxy-D-ribo-hexitol 
• 111967-29-4 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-gluco-heptitol 
• 111967-30-7 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-xylo-hexitol 
• 82109-99-7 (2S,3S,5S)-5-hydroxymethyl-2-methyltetrahydrofuran-3-ol 
• 41341-99-5 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 124251-98-5 (S)-3-(2-Benzyloxy-ethoxy)-1-diazo-butan-2-one 
• 123990-91-0 (S)-5-Benzyloxymethyl-2-methyl-dihydro-furan-3-one 

Downstream Products

• 2303-35-7 (+)-muscarine chloride 
• 82083-43-0 (+)-muscarine toluene-p-sulfonate salt 
• 111967-25-0 L-(+)-epimuscarine toluene-p-sulphonate 
• 24570-49-8 (+)-muscarine iodide 

Relevant academic research and scientific papers

Blue light photoredox decarboxylation and tin-free Barton-McCombie reactions in the stereoselective synthesis of (+)-muscarine

Starting from a 1,2-O-isopropylidene-α-D-xylofuranose derivative, a non-toxic free-radical approach for the synthesis of (+)-muscarine is reported. To this end, a stereoselective allylation reaction at the anomeric position of a respective xylofuranose de

A Practical Synthesis of (+)-Muscarine from L-Rhamnose

A practical seven-step synthesis of muscarine tosylate (trimethyl)ammonium tosylate> from L-rhamnose is described, which does not require the use of any protecting group.

(+)-Muscarine From L-Rhamnose

A short synthesis of (+)-muscarine from L-rhamnose which does not require the use of any protecting group is described.

A Concise Enantioselective Synthesis of (+)-Muscarine from (R)-O-Benzylglycidol

A concise enantioselective synthesis of (+)-muscarine has been established via the novel formation of a 3,4-dihydrofuran starting from (R)-O-benzylglycidol.

Dichloromethylenation of Sugar γ-Lactones: a Stereospecific Synthesis of L-(+)-Muscarine and L-(+)-Epimuscarine Toluene-p-sulphonates

Treatment of di-isopropylidene-D-mannono-1,4-lactone (3) with hexamethylphosphorous triamide-tetrachloromethane gave the dichloro-olefin (4), which was converted into the ketone (5) by treatment with lithium di-isopropylamide.Reduction with Raney nickel g

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.