Synthesis of protected p-methoxyphenyl D-galactopyranosyl(α1→4)-(D-galactopyranosyl)-(β1→3)-2-deoxy-2-acetamido-D-glucopyranoside
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Department of Organic Chemistry,School of Pharmacy,Second Military Medical University,Department of Organic Chemistry,School of Pharmacy,Second Military Medical University,Department of Organic Chemistry,School of Pharmacy,Second Military Medical University,Department of Organic Chemistry,School of Pharmacy,Second Military Medical University,Department of Organic Chemistry,School of Pharmacy,Second Military Medical University

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Supported by Major Science and Technology Project of China (2012ZX09502001-005, 2011ZXJ09201-012) and Youth Project of National Natural Science Foundation of China (21202200).

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    Abstract:

    Objective To synthesize fully protected p-methoxyphenyl D-galactopyranosyl(α1→4)-(D-galactopyranosyl)-(β1→3)-2-deoxy-2-acetamido-D-glucopyranoside. Methods With D-galactose and D-glucosamine hydrochloride used as the initial compounds, we stereoselectively and efficiently synthesized p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl (α1→4)-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-(β1→3)-6-benzyl-2-deoxy-2-acetamido-β-D-glucopyranoside (1) by glucosinolates glycosylation and Schmidt glycosylation. Results Our method efficiently produced the target compound, and the structures of the main intermediates and target compound were confirmed by 1HMNR, 13CMNR and MS. Conclusion We have established a simple synthesis method with high universal property for target compound; additionally, the protective base is easily removable. Our method is applicable for the synthesis of various oligosaccharides.

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History
  • Received:September 28,2015
  • Revised:November 23,2015
  • Adopted:December 29,2015
  • Online: February 26,2016
  • Published:
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