82083-43-0

Upstream product

• 41341-99-5 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 111967-29-4 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-allo-heptitol 
• 112020-37-8 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-ribo-hexitol 
• 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 
• 75499-84-2 2,5-anhydro-4,6-di-O-benzoyl-1,3-di-O-p-tolylsulphonyl-D-glucitol 
• 75499-85-3 2,5:3,4-dianhydro-1-O-p-tolylsulphonyl-D-allitol 
• 20031-16-7 L-Rhamnono-1,4-lactone 
• 138480-28-1 2-O-methanesulfonyl-L-rhamnono-1,4-lactone 
• 138480-29-2 2-O-methanesulfonyl-3,6-dideoxy-L-erythro-hex-2-enono-1,4-lactone 
• 138480-30-5 2-O-methanesulfonyl-3,6-dideoxy-L-arabino-hexono-1,4-lactone 
• 6014-42-2 L-rhamnose 

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.

Stereocontrolled preparation of tetrahydrofurans from acid-promoted rearrangements of allylic acetals

A new method for constructing substituted tetrahydrofurans from readily available allylic did and carbonyl components is reported (eq 1). This synthesis is highly stereocontrolled and allows carbon side chains to be incorporated at each carbon. Enantiomer

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.