title: Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose.
abstract: Oligosaccharide syntheses are an important source of well-defined sugar constructs particularly needed for the evaluation of structure-activity relationships. The chemical assembly of oligosaccharides requires several building blocks, that is, glycosyl donors and acceptors, which are prepared in multistep processes and in a generally tedious and time-consuming manner. Having developed one-pot procedures meant to minimise the effort in sugar building block preparation, we tackled herein the one-pot preparation of fully protected and 2-, 3-, 4-, and 6-alcohol derivatives of d-mannose, a widely distributed monosaccharide. As a consequence of the hydroxyl group pattern of D-mannose, regioselective and stereoselective benzylidenations were developed and later seamlessly utilised as the first transformation in the one-pot procedure.
authors: Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei 115, Taiwan.
authors: Pratap S
authors: PS
authors: Patil
authors: Chia-Chen
authors: CC
authors: Lee
authors: Yu-Wen
authors: YW
authors: Huang
authors: Medel Manuel L
authors: MM
authors: Zulueta
authors: Shang-Cheng
authors: SC
authors: Hung
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001597:Benzylidene Compounds; D009844:Oligosaccharides; D008358:Mannose