82109-99-7

Upstream product

• 111080-07-0 (4S,5S)-2,2,4-Trimethyl-5-(R)-1-oxiranylmethyl-[1,3]dioxolane 
• 111967-27-2 anhydro-1,4-dideoxy-D-gluco-heptitol 
• 111967-30-7 2,5-anhydro-3-O-benzoyl-1,4-dideoxy-D-xylo-hexitol 
• 82109-98-6 Benzoic acid (2S,4S,5S)-4-hydroxy-5-methyl-tetrahydro-furan-2-ylmethyl ester 
• 949932-83-6 C₁₃H₁₈O₃ 
• 123990-91-0 (S)-5-Benzyloxymethyl-2-methyl-dihydro-furan-3-one 
• 124251-98-5 (S)-3-(2-Benzyloxy-ethoxy)-1-diazo-butan-2-one 
• 124251-97-4 (S)-2-(2-Benzyloxy-ethoxy)-propionic acid 
• 110134-89-9 (S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propan-2-ol 
• 110134-87-7 Formic acid (1S,3S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-4-oxo-pentyl ester 
• 110134-81-1 (S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one 
• 110134-83-3 (S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3-methyl-tetrahydro-pyran-4-ol 
• 110134-82-2 (S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2,4-diol 
• 110134-86-6 (2S,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-3,4-dihydro-2H-pyran-4-ol 

Downstream Products

• 75499-91-1 2,5-anhydro-1,4-dideoxy-6-O-(p-tolylsulphonyl)-D-xylo-hexitol 
• 111967-25-0 L-(+)-epimuscarine toluene-p-sulphonate 

Relevant academic research and scientific papers

Efficient chirality transfer in the Sml2-mediated cyclization of aldehydo β-alkoxyvinyl sulfoxides: Asymmetric synthesis of 3-hydroxyoxanes

Stereoselective syntheses of 3-hydroxyoxanes were achieved via efficient chirality transfer in the Sml2-mediated cyclization reactions of aldehydo β-alkoxyvinyl sulfoxides.

Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine

The stereoselective synthesis of tetrahydrofurans was achieved by formal [3+2]-cycloaddition of allyl and crotylsilanes with α-triethylsilyloxy aldehydes. The scope of the reaction was examined by using different α-substituted aldehydes and different subs

Practical chiral route to muscarine and its three diastereomers

A practical route to all possible stereoisomers of the muscarine alkaloids in optically pure forms has been developed starting from a readily accessible chiral starting material.

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.