New entry for asymmetric deoxyazasugar synthesis: syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin

Asano, Koji; Hakogi, Toshikazu; Iwama, Seiji; Katsumura, Shigeo

doi:10.1039/a807532h

Cited by 38 publications

(17 citation statements)

References 9 publications

(4 reference statements)

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“…The protected compounds were prepared by introducing the amino function by nucleophilic ring opening of an epoxide or a cyclic sulfate obtained from the key intermediate 11, which is readily accessible by Sharpless asymmetric epoxidation of 2,4-pentadien-1-ol. 47 This intermediate has been widely used for the synthesis of various iminosugars 17,[48][49][50] including our recent synthesis of DAJNAc (9). 42 Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors

et al. 2015

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2-Acetamido-1,2-dideoxyiminosugars are selective and potent inhibitors of hexosaminidases and therefore show high therapeutic potential for the treatment of various diseases, including several lysosomal storage disorders. A stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc), the iminosugar analog of N-acetylglucosamine, with high overall yield is here described. This novel procedure further allowed accessing ureidoDNJNAc conjugates through derivatization of the endocyclic amine on a key pivotal intermediate. Remarkably, some of the ureido-DNJNAc representatives behaved as potent and selective inhibitors of β-hexosaminidases, including the human enzyme, being the first examples of neutral sp 2 -iminosugar-type inhibitors reported for these enzymes. Moreover, the amphiphilic character of the new ureido-DNJNAc is expected to confer better drug-like properties.

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Section: Resultsmentioning

confidence: 99%

Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors

et al. 2015

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“…Katsumura et al also outlined the syntheses for both 1-deoxygalactostatin 217 and 1-deoxyaltronojirimycin 218 from the key bicyclic oxazolidinylpiperidine intermediate 108 (Schemes 8 and 27). 84 Shilvock and Fleet reported the synthesis of 1-deoxygalactostatin via a stannane mediated hydroxymethylation of 5-azido-L L-lyxono-1,4-lactone 242 (Scheme 28). 116 From the transmetallation of the stannylmethanol species 243, the hydroxymethyllithium compound 244 was derived.…”

Section: The Synthesis Of 1-deoxygalactostatin and 1-deoxyaltronojirimentioning

confidence: 99%

“…103 (Scheme 8). 84,85 The reaction of 103 with the lithium anion of propargyl alcohol silyl ether gave ketone 104. A stereoselective reduction with diisobutylaluminium 2,6-di-tert-butyl-4-methylphenoxide produced the desired anti alcohol 105 in 92% yield.…”

Section: Noncarbohydrate Routes To 1-deoxynojirimycin (Dnj)mentioning

confidence: 99%

Recent advances in the chemistry of azapyranose sugars

Afarinkia

Bahar

2005

Tetrahedron: Asymmetry

230

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“…Direct dihydroxylation of 205 with osmium tetroxide introduced a cis -diol moiety oriented anti to the tert -butyldimethylsilyloxy group and basic hydrolysis of 208 gave (2 S ,3 S ,4 S ,5 S )-2-(hydroxymethyl)piperidine-3,4,5-triol ((2 S ,3 S ,4 S ,5 S )- 200 , ʟ-1-deoxymannojirimycin). After removal of the silyl protection from 205 the epoxidation with MCPBA produced the syn -epoxide 209 which was converted into (2 S ,3 S ,4 R ,5 S )-2-(hydroxymethyl)piperidine-3,4,5-triol ((2 S ,3 S ,4 R ,5 S )- 200 , ʟ-1-deoxyaltronojirimycin) as described earlier [111].…”

Section: Reviewmentioning

confidence: 99%

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

Głowacka¹,

Trocha²,

Wróblewski³

et al. 2019

Beilstein J. Org. Chem.

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Since Garner’s aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of N-(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.

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New entry for asymmetric deoxyazasugar synthesis: syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin

Cited by 38 publications

References 9 publications

Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors

Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors

Recent advances in the chemistry of azapyranose sugars

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

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