((4R,5S)-4-{(4R,5S)-5-[(E)-8-(2-Hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester | 397870-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((4R,5S)-4-{(4R,5S)-5-[(E)-8-(2-Hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(4R,5S)-4-[(4R,5S)-5-[(E)-8-(2-hexyl-1,3-dioxolan-2-yl)oct-1-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-yl]carbamate
• CAS: 397870-75-6
• 化学式: C₃₄H₆₁NO₉
• 分子量: 627.86
• InChiKey: WJJVTJUXBGNUJI-VPDPOGRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ((4R,5S)-4-{(4R,5S)-5-[(E)-8-(2-Hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (2S,3R,4R)-2-acetamido-3-acetoxy-2-acetoxymethyl-4-((E,S)-1-acetoxy-10-oxohexadec-2-en-1-yl)-4-butanolide
  参考文献：
  名称：

  Total Synthesis of Sphingofungin E from d-Glucose

  摘要：

  Total synthesis of sphingofungin E (1) Is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized part in sphingofungin E (4) stereoselectively. Coupling reaction of 4 with the C-12 hydrophobic part, followed by further manipulation, completed the total synthesis.

  DOI：

  10.1021/ol0171620
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose 在 盐酸 、 正丁基锂 、 zinc(II) tetrahydroborate 、 草酰氯 、 萘 、 camphor-10-sulfonic acid 、 lithium 、 二异丁基氢化铝 、 二正丁基氧化锡 、 碳酸氢钠 、 臭氧 、 二甲基亚砜 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 生成 ((4R,5S)-4-{(4R,5S)-5-[(E)-8-(2-Hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Total Synthesis of Sphingofungin E from d-Glucose

  摘要：

  Total synthesis of sphingofungin E (1) Is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized part in sphingofungin E (4) stereoselectively. Coupling reaction of 4 with the C-12 hydrophobic part, followed by further manipulation, completed the total synthesis.

  DOI：

  10.1021/ol0171620

文献信息

• Total Synthesis of Sphingofungin E from <scp>d</scp>-Glucose
  作者：Takeshi Oishi、Koji Ando、Kenjin Inomiya、Hideyuki Sato、Masatoshi Iida、Noritaka Chida

  DOI：10.1021/ol0171620

  日期：2002.1.1

  Total synthesis of sphingofungin E (1) Is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized part in sphingofungin E (4) stereoselectively. Coupling reaction of 4 with the C-12 hydrophobic part, followed by further manipulation, completed the total synthesis.