(2S,4R)-1-[(4R,6R)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-5-{(4S,6S)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-((4R,5R)-2,2-dimethyl-4-pentyl-[1,3]dioxan-5-yl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentane-2,4-diol | 309755-06-4

• 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: (2S,4R)-1-[(4R,6R)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-5-{(4S,6S)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-((4R,5R)-2,2-dimethyl-4-pentyl-[1,3]dioxan-5-yl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentane-2,4-diol
• 英文别名: (2S,4R)-1-[(4S,6S)-6-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(4R,5R)-2,2-dimethyl-4-pentyl-1,3-dioxan-5-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-5-[(4R,6R)-2,2-dimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]pentane-2,4-diol
• CAS: 309755-06-4
• 化学式: C₄₅H₈₀O₁₀Si
• 分子量: 809.21
• InChiKey: BWJFPJKXAKBGKU-IKDGPZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  56
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (2S,4R)-1-[(4R,6R)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-5-{(4S,6S)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-((4R,5R)-2,2-dimethyl-4-pentyl-[1,3]dioxan-5-yl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentane-2,4-diol 在 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 以95%的产率得到tert-butyl-[(1S)-1-[(4R,5R)-2,2-dimethyl-4-pentyl-1,3-dioxan-5-yl]-2-[(4S,6S)-6-[[(4S,6R)-6-[[(4S,6R)-2,2-dimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethoxy]-dimethylsilane
  参考文献：
  名称：

  An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions

  摘要：

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01289-2
• 作为产物：
  描述：

  (4R,5R)-5-formyl-2,2-dimethyl-4-pentyl-1,3-dioxane 在 N-(p-toluenesulfonyl)-L-valine 、 sodium tetrahydroborate 、 草酰氯 、 (S)-oxazaborolidinone derived from BH₃*THF 、 camphor-10-sulfonic acid 、 二乙基甲氧基硼烷 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 14.0h， 生成 (2S,4R)-1-[(4R,6R)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-5-{(4S,6S)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-((4R,5R)-2,2-dimethyl-4-pentyl-[1,3]dioxan-5-yl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentane-2,4-diol
  参考文献：
  名称：

  An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions

  摘要：

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01289-2

文献信息

• An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions
  作者：Syun-ichi Kiyooka、Mostofa A Hena、Tomomi Yabukami、Kazunori Murai、Fumitaka Goto

  DOI：10.1016/s0040-4039(00)01289-2

  日期：2000.9

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.