27958-06-1

Usage

Uses

Used in Pharmaceutical Industry:
Deacetylanisomycin is used as an antimalarial agent, inhibiting the growth of P. falciparum strains K1 and T9-96 in vitro. It also exhibits cytotoxicity against LU99 lung carcinoma and MCF-7 breast cancer cells, making it a potential candidate for anticancer drug development.
Used in Agricultural Industry:
Deacetylanisomycin serves as an agricultural fungicide, leveraging its potent inhibitory effects on protein synthesis to control fungal growth and protect crops.
Used in Research Applications:
Deacetylanisomycin is utilized as a negative control for assessing protein synthesis inhibitor activity in molluscan neurons, providing a benchmark for evaluating the effectiveness of other potential inhibitors in biological research.

InChI:InChI=1/C12H17NO3/c1-16-9-4-2-8(3-5-9)6-10-12(15)11(14)7-13-10/h2-5,10-15H,6-7H2,1H3/t10-,11+,12+/m0/s1

Upstream product

• 115828-77-8 (2R,3S,4S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyl)-pyrrolidine 
• 100449-58-9 (2R,3S,4S)-2-(4-methoxybenzyl)-3,4-O-bis-(methoxymethyl)pyrrolidine 
• 228396-56-3 {(1R)-1-(N-tert-butoxycarbonylamino)-1-deoxy-1-(p-methoxybenzyl)-2,3-O-isopropylidene-4-chloro-L-threitol} 
• 115828-74-5 2,3-di-O-benzyl-5-deoxy-5-C-(4-methoxyphenyl)-L-arabinose (E,Z)-oxime 
• 115828-69-8 ethyl (5R,S)-2,3-di-O-benzyl-5-C-(4-methoxyphenyl)-α-L-arabinofuranoside 
• 3969-59-3 mannitol triacetonide 
• 172330-70-0 (3R,4S,5S)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 1054695-76-9 (2S,3S,4S,5R)-5-Benzylamino-1,3,4-tris-benzyloxy-6-(4-methoxy-phenyl)-hexan-2-ol 
• 172330-68-6 (3R,4S,5R)-1-Benzyl-3,4-bis-benzyloxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 293314-32-6 (2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol 
• 478623-19-7 ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 478623-18-6 ethyl (2R,3S,4R)-4-(tert-butoxycarbonyl)amino-2,3-dihydroxy-5-(4-methoxyphenyl)pentanoate 
• 478623-20-0 (1R,4R,5R)-1-[N-(tert-butoxycarbonyl)]-1-(5-bromomethyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxyphenyl)ethan-1-amine 
• 478623-17-5 ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate 

Downstream Products

• 27958-05-0 (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 82916-86-7 N-((benzyloxy)carbonyl)-3β,4α-dihydroxy-2β-(p-methoxybenzyl)pyrrolidine 
• 111602-18-7 (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester 
• 21497-40-5 (+/-)-anisomycin 
• 111765-92-5 (2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 

Relevant academic research and scientific papers

A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars

A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-D-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-L-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields.

Practical synthesis of trans-dihydroxybutyrolactols as chiral C4 building blocks and their application to the synthesis of polyhydroxylated alkaloids

Practical syntheses of trans-dihydroxybutyrolactols 2a, 2b and 2c from inexpensive chiral pool compounds l-ascorbic, d- and l-tartaric acid have been achieved on a multigram-scale. The synthetic applications of these chiral building blocks have been demonstrated in the efficient total or formal synthesis of polyhydroxylated alkaloids (+)-lentiginosine and (-)-deacetylanisomycin in concise routes. The Royal Society of Chemistry 2013.

A new approach to (+)-anisomycin

An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.

Stereoselective synthesis of (-)-deacetylanisomycin

A stereoselective synthesis of (-)-deacetylanisomycin has been achieved from a nitrone derived from 1-threose in 6 steps and 53.7% overall yield, The key step of the synthesis is the nucleophilic addition of a Grignard derivative with complete diastereofacial selectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes

Representative diastereomeric, erythritol and threitol polyhydroxylated pyrrolidine imine scaffolds have been rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic (RM) additions (R = Me, Et, allyl, hex

An efficient synthesis of (-)-deacetylanisomycin starting from D-tyrosine1

The antibiotic (-)-deacetylanisomycin was synthesized starting from D-tyrosine using Sharpless asymmetric dihydroxylation as a key reaction.

Stereoselective synthesis of (-)-deacetylanisomycin

A concise synthesis of (-)-deacetylanisomycin has been achieved via the stereocontrolled reductive alkylation of a protected trihydroxynitrile derived from tartaric acid. The resulting aminotriol was selectively O-mesylated on the primary hydroxyl group a

A novel, concise and highly efficient stereospecific synthesis of deacetylanisomycin

A practical and highly stereospecific synthesis of deacetylanisomycin has been achieved via the addition of p-methoxybenzylmagnesiumchloride to (Z)-N-(4-O-benzyl- 1-deoxy-2,3-O-isopropylidene-L-yliden)benzyl amine-N- oxide in an efficient manner.

A SHORT SYNTHETIC APPROACH TO ENANTIOMERICALLY PURE (-)-ANISOMYCIN

A convenient enantiomerically pure route to an antibiotic, natural (-)-anisomycin has been developed in a short number of steps by featuring the stereocontrolled elaboration of the fuctionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-β-L-arabin