ethyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside | 1269776-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside
• CAS: 1269776-99-9
• 化学式: C₅₆H₆₂O₉S
• 分子量: 911.169
• InChiKey: ISWHKHHXVUBNKZ-TVRAFFIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  66.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ethyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside 、 octyl (4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到octyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the hexasaccharide repeating unit corresponding to the cell wall lipopolysaccharide of Azospirillum irakense KBC1

  摘要：

  A convenient chemical synthesis of the hexasaccharide repeating unit of the cell wall lipopolysaccharide of Azospirillum irakense KBC1 has been successfully achieved. A stereo- and regioselective [4 + 2] block glycosylation strategy has been used to obtain the target hexasaccharide as its octyl glycoside. All synthetic intermediates have been prepared in high yields from commercially available reducing sugars following a series of protection-deprotection reactions. An oxidation-reduction methodology has been applied to convert beta-D-glucosidic unit to a beta-D-mannosidic moiety. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.008
• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl trichloroacetimidate 、 ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到ethyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the hexasaccharide repeating unit corresponding to the cell wall lipopolysaccharide of Azospirillum irakense KBC1

  摘要：

  A convenient chemical synthesis of the hexasaccharide repeating unit of the cell wall lipopolysaccharide of Azospirillum irakense KBC1 has been successfully achieved. A stereo- and regioselective [4 + 2] block glycosylation strategy has been used to obtain the target hexasaccharide as its octyl glycoside. All synthetic intermediates have been prepared in high yields from commercially available reducing sugars following a series of protection-deprotection reactions. An oxidation-reduction methodology has been applied to convert beta-D-glucosidic unit to a beta-D-mannosidic moiety. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.008