87796-27-8

Basic information

• Product Name: 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-allitol
• Synonyms: 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-allitol
• CAS NO: 87796-27-8
• Molecular Weight: 312.363
• Mol File: 87796-27-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-allitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-allitol(87796-27-8)
• EPA Substance Registry System: 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-allitol(87796-27-8)

Safety Data

• Hazardous Substances Data: 87796-27-8(Hazardous Substances Data)

Upstream product

• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 99300-02-4 1,5-dideoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-2-O-methylsulphonyl-5-phthalimido-D-ribitol 
• 99394-31-7 (2R,3S,4R)-3,4-dihydroxy-2-(p-methoxybenzyl)pyrrolidine hydrochloride 
• 933992-79-1 (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine 
• 99284-55-6 5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-L-ribonolactone 
• 99284-48-7 2,5-anhydro-1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-ribitol 
• 1964-58-5 (2R,3S,4R)-3,4-epoxy-2-(p-methoxybenzyl)pyrrolidine 
• 87796-36-9 (E,Z)-5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-L-ribose oxime 
• 87859-50-5 (2R,3S,4R)-3,4-isopropylidenedioxy-2-(p-methoxybenzyl)-pyrrolidine 
• 87796-34-7 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-2,5-di-O-methylsulphonyl-D-ribitol 
• 87796-48-3 (2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine 
• 87796-40-5 5-deoxy-2,3-O-isopropylidene-4-O-methylsulphonyl-5-(p-methoxyphenyl)-L-ribononitrile 
• 87796-46-1 (2R,3S,4S)-4-allyloxy-3-hydroxy-2-(p-methoxybenzyl)-pyrrolidine 
• 87796-31-4 1-deoxy-3,4-O-isopropylidene-1-(-p-methoxyphenyl)-d-ribitol 
• 22862-76-6 (-)-anisomycin 

Relevant articles and documents

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 .