2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-β-D-psicofuranoside | 1242059-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-β-D-psicofuranoside
• CAS: 1242059-08-0
• 化学式: C₄₀H₄₆O₁₁
• 分子量: 702.799
• InChiKey: VWJSBVZMGCSSSY-XEQXMXHRSA-N

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-β-D-psicofuranoside 在 10% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以100%的产率得到α-D-mannopyranosyl-β-D-psicofuranoside
  参考文献：
  名称：

  Chemical synthesis of β-d-psicofuranosyl disaccharides

  摘要：

  Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 23,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting a-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and et-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.030
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl 1,6-di-O-benzoyl-β-D-psicofuranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-β-D-psicofuranoside
  参考文献：
  名称：

  Chemical synthesis of β-d-psicofuranosyl disaccharides

  摘要：

  Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 23,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting a-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and et-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.030