99340-35-9

Upstream product

• 87796-37-0 (E,Z)-5-deoxy-2,3-O-isopropylidene-5-phenyl-L-ribose oxime 
• 99284-56-7 (2R,3S,4R)-2-benzyl-3,4-dihydroxypyrrolidine hydrochloride 
• 87810-06-8 Acetic acid (2R,3S,4S)-4-allyloxy-1,2-dibenzyl-pyrrolidin-3-yl ester 
• 87796-41-6 5-deoxy-2,3-O-isopropylidene-4-O-methylsulphonyl-5-phenyl-L-ribononitrile 
• 87796-28-9 1-deoxy-3,4-O-isopropylidene-1-phenyl-D-allitol 
• 87796-30-3 5-deoxy-2,3-O-isopropylidene-5-phenyl-β-L-ribofuranose 
• 87796-47-2 (2R,3S,4S)-4-allyloxy-2-benzyl-3-hydroxypyrrolidine 
• 87859-53-8 (2R,3S,4R)-2-benzyl-3,4-epoxypyrrolidine 
• 100-44-7 benzyl chloride 
• 249617-10-5 2-benzyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 249617-05-8 (2R,3S,4S)-1,2-Dibenzyl-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)pyrrolidine 
• 249617-03-6 Benzyl-[(1R,2S)-1-benzyl-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-amine 
• 249617-07-0 (2R,3S,4S)-2-Benzyl-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypyrrolidine 
• 186465-28-1 (2S,3S,4R)-4-(Benzylamino)-3-(benzyloxy)-5-phenylpentane-1,2-diol 

Relevant academic research and scientific papers

Stereoselective synthesis and biological evaluation of anisomycin and 2- substituted analogues

The naturally occurring pyrrolidine anisomycin 1, its deacetyl derivative 9k, and some previously unknown analogues were prepared from 2-O- benzyl-3,4-O-isopropylidene-L-threose 2, via the N-benzylimine 3, using highly threo-selective additions of organol

A New Synthesis of (-)-Anisomycin and its Demethoxy analogue from D-Ribose

2,3-O-Isopropylidene-D-ribose (7) reacted with p-methoxybenzylmagnesium chloride in tetrahydrofuran to give the D-allotriol (6a) (77percent).Periodate oxidation of compound (6a) followed by reaction with hydroxylamine hydrochloride in pyridine gave (E,Z)-5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-L-ribose oxime (18a) which was converted into the nitrile methanesulphonate (19a) with methanesulphonyl chloride in pyridine.Reduction of the nitrile (19a) with lithium aluminium hydride gave (2R,3S,4R)-3,4-isopropylidenedioxy-2-(p-methoxybenzyl)pyrrolidine (2a) , which was converted into the epoxide (24a) (68percent) via the bromo acetates (28a) and (29a).Regioselective opening of the epoxide ring in compound (24a) with acidic allyl alcohol gave the allyl ether (30a) (63percent) which was converted into the N-benzyl 3-acetoxy compound (31a) (77percent).Removal of the allyl and benzyl groups, by treatment with palladium-charcoal under acidic conditions followed by hydrogenolysis, gave (-)-anisomycin (1a (86percent). A similar series of reactions afforded demethoxyanisomycin (1b) which showed antibiotic activity against Trichomonas vaginalis .