p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside | 333717-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside
• 英文别名: (3aS,4S,6R,6aS)-4-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-6-[(1R)-1-phenylmethoxybut-3-enyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 333717-21-8
• 化学式: C₂₆H₃₂O₆
• 分子量: 440.536
• InChiKey: OSVNOWWWTVUFHB-VAFBSOEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside 在 palladium on activated charcoal 盐酸 、 9-borabicyclo[3.3.1]nonane dimer 、 甲酸 、 草酰氯 、 iodonium(di-γ-collidine) perchlorate 、 4 Angstroem MS 、 甲酸铵 、 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 33.0h， 生成 八倾吲嗪三醇
  参考文献：
  名称：

  Allylated Monosaccharides as Precursors in Triple Reductive Amination Strategies:  Synthesis of Castanospermine and Swainsonine

  摘要：

  The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.

  DOI：

  10.1021/jo001447t
• 作为产物：
  描述：

  在 sodium periodate 、 三氟化硼乙醚 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside
  参考文献：
  名称：

  Allylated Monosaccharides as Precursors in Triple Reductive Amination Strategies:  Synthesis of Castanospermine and Swainsonine

  摘要：

  The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.

  DOI：

  10.1021/jo001447t

文献信息

• Allylated Monosaccharides as Precursors in Triple Reductive Amination Strategies:  Synthesis of Castanospermine and Swainsonine
  作者：Hang Zhao、Sunej Hans、Xuhong Cheng、David R. Mootoo

  DOI：10.1021/jo001447t

  日期：2001.3.1

  The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.