octyl 2,6-di-O-benzyl-β-D-galactopyranoside | 1269776-88-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-6-octoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 1269776-88-6
• 化学式: C₂₈H₄₀O₆
• 分子量: 472.622
• InChiKey: ZYIJTPKMCNZOFD-QBROEMLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  octyl 2,6-di-O-benzyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 、 水 、 对甲苯磺酸 、 原乙酸三乙酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 octyl [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：

  正辛基Β-D-吡喃半乳糖苷 在 水 、 对甲苯磺酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 octyl 2,6-di-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

文献信息

• Synthesis of the hexasaccharide repeating unit corresponding to the cell wall lipopolysaccharide of Azospirillum irakense KBC1
  作者：Samir Ghosh、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2010.11.008

  日期：2010.12

  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.