Literature DB >> 14602037

A novel sulfonamidoglycosylation of glycals.

Pedro A Colinas1, Rodolfo D Bravo.   

Abstract

[reaction: see text] The sulfonamidoglycosylation of benzylated glycals using a catalytic amount of triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the beta anomers with good to high yields. This process was demonstrated with d-galactal and d-glucal. Two of the new N-2-(deoxyglycosyl)sulfonamides were tested as inhibitors of tumor cell growth in vitro and showed antiproliferative properties in the micromolar range.

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Year:  2003        PMID: 14602037     DOI: 10.1021/ol035838g

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Catalytic intermolecular hydroamination of vinyl ethers.

Authors:  Nirmal K Pahadi; Jon A Tunge
Journal:  Synlett       Date:  2009-12-01       Impact factor: 2.454

2.  Self-promoted and stereospecific formation of N-glycosides.

Authors:  Michael Martin Nielsen; Patrycja Mała; Eirikur Þórir Baldursson; Christian Marcus Pedersen
Journal:  Chem Sci       Date:  2019-04-18       Impact factor: 9.825

3.  Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings.

Authors:  G A Bradshaw; A C Colgan; N P Allen; I Pongener; M B Boland; Y Ortin; E M McGarrigle
Journal:  Chem Sci       Date:  2018-10-22       Impact factor: 9.825

  3 in total

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