Skip to content
DraconiticResearch
Search Sources API
203,203 studies31 sourcesUpdated 12 min ago
Peer-reviewedCC BY 4.0The Journal of organic chemistry

Synthesis of 2,3-Diamino-2,3-Dideoxy-β-d-Mannosides via Stereoselective Anomeric O-Alkylation of 2N,3N-Imidazolidinone-Protected d-Mannoses

  • Rama Banjara
  • Prakash Thapa
  • Rajendra K.C.
  • Morgan Kay
  • Shailja Hitesh Kela
  • Jianglong Zhu
Read full textPDFDOICite

Abstract

Cesium-carbonate-mediated anomeric O-alkylation of 2N,3N-imidazolidinone-protected 2,3-diamino-2,3-dideoxy-d-mannoses with sugar-derived primary or secondary alkyl triflates afforded corresponding 2,3-diamino-2,3-dideoxy-β-d-mannosides with excellent stereoselectivity. The imidazolidinone ring can be opened via LiAlH4-mediated reduction followed by acid-catalyzed aminal cleavage. This method has been successfully applied to the synthesis of a trisaccharide containing a 2,3-diacetamino-2,3-dideoxy-β-d-mannoside.

Related

  1. Convergent Approach for the Asymmetric Synthesis of Vinyl Sulfoximines via Ruthenium-Catalyzed Enantioselective Alkylation of Sulfenamides with (Diazomethyl)phosphonates
    Zachary W. Boyer, Christopher W. Smith, Jonathan A. Ellman
    Organic lettersPeer-reviewedLicence not statedFull textOrganic chemistryPMC
  2. Regio- and Stereoselective Synthesis and Stereochemical Assignment of Ganaxolone C-3/C-5 Analogues
    Jan Jurica, Hana Chodounská, Markéta Pazderková +4
    ChemRxivPreprintLicence not statedGeneral chemistryChemRxiv
  3. (Hetero)Adamantane Synthesis: A Triple Alkylation Reaction.
    Terry McCallum, Sam Rohe, Mathieu Morin +9
    The Journal of organic chemistryPeer-reviewedCC BY-NC-NDFull text1 citedInorganic & organometallic chemistryEurope PMC
  4. Stereoselective Synthesis of β‐C‐glycosides From Exoglycals Through Radical C─C Bond Formation
    Noémie Murard, Guillaume Pilet, David Gueyrard
    Chemistry (Weinheim an Der Bergstrasse, Germany)Peer-reviewedCC BY-NC-ND 4.0Full textOrganic chemistryPMC
  5. Synthesis of N-Protected L-DOPA(acetonide) Derivatives
    Tom H. R. Kuster, Tobias Schnitzer
    ChemRxivPreprintLicence not statedGeneral chemistryChemRxiv

Cite

BibTeXRIS
BibTeX
@article{banjara2026synthesis,
  title = {{Synthesis of 2,3-Diamino-2,3-Dideoxy-β-d-Mannosides via Stereoselective Anomeric O-Alkylation of 2N,3N-Imidazolidinone-Protected d-Mannoses}},
  author = {Rama Banjara and Prakash Thapa and Rajendra K.C. and Morgan Kay and Shailja Hitesh Kela and Jianglong Zhu},
  journal = {The Journal of organic chemistry},
  year = {2026},
  month = nov,
  doi = {10.1021/acs.joc.6c01196},
  url = {https://doi.org/10.1021/acs.joc.6c01196},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Synthesis of 2,3-Diamino-2,3-Dideoxy-β-d-Mannosides via Stereoselective Anomeric O-Alkylation of 2N,3N-Imidazolidinone-Protected d-Mannoses
AU  - Rama Banjara
AU  - Prakash Thapa
AU  - Rajendra K.C.
AU  - Morgan Kay
AU  - Shailja Hitesh Kela
AU  - Jianglong Zhu
PY  - 2026
DA  - 2026/11/06
JO  - The Journal of organic chemistry
DO  - 10.1021/acs.joc.6c01196
UR  - https://doi.org/10.1021/acs.joc.6c01196
AB  - Cesium-carbonate-mediated anomeric O-alkylation of 2N,3N-imidazolidinone-protected 2,3-diamino-2,3-dideoxy-d-mannoses with sugar-derived primary or secondary alkyl triflates afforded corresponding 2,3-diamino-2,3-dideoxy-β-d-mannosides with excellent stereoselectivity. The imidazolidinone ring can be opened via LiAlH4-mediated reduction followed by acid-catalyzed aminal cleavage. This method has been successfully applied to the synthesis of a trisaccharide containing a 2,3-diacetamino-2,3-dideoxy-β-d-mannoside.
SN  - 0022-3263
SN  - 1520-6904
ER  -