3-((6S,7R)-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl)propanal | 213964-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((6S,7R)-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl)propanal
• 英文别名: 3-[(6S,7R)-7-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl]propanal
• CAS: 213964-79-5
• 化学式: C₂₁H₄₀O₄Si
• 分子量: 384.632
• InChiKey: DMDNAKXMSGRXGD-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((6S,7R)-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl)propanal 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 四丙基高钌酸铵 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 sodium cyanoborohydride 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 43.17h， 生成 2-((6S,7R)-6-(3-(benzyl(tert-butoxycarbonyl)amino)propyl)-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-7-yl)acetic acid
  参考文献：
  名称：

  Structure–activity relationships of the truncated norzoanthamines exhibiting collagen protection toward anti-osteoporotic activity

  摘要：

  The marine alkaloid norzoanthamine is a candidate drug for osteoporosis treatment. Due to its structural complexity, simplified analogues possessing similar biological activities are needed for further research. Recently, we found that the bisaminal unit, representing two-thirds of the original structure, is a bioactive equivalent. We synthesized three kinds of further truncated norzoanthamines and evaluated their collagen protection activities. No analog with collagen protection activity comparable to that of the bisaminal unit was found. Thus, we confirmed the importance of the bisaminal unit for the collagen protection activity. Furthermore, we found that the recognition tolerance of the substrate collagen is relatively large by comparing both enantiomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.040
• 作为产物：
  描述：

  (4aS,8aS)-5-Hydroxy-4a,8a-dimethyl-hexahydro-naphthalene-1,6-dione 在 咪唑 、 lead(IV) acetate 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 双氧水 、 二异丁基氢化铝 、 sodium amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 22.25h， 生成 3-((6S,7R)-7-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6,7-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl)propanal
  参考文献：
  名称：

  zoanthamine / norzoanthamine生物碱的合成研究：杂环胺核心的高级中间体

  摘要：

  以对映体和立体选择性的方式制备了先进的中间体，用于制备藏菊胺基间氮杂胺生物碱的杂环氨基核。利用立体选择性铜酸盐添加到容易获得的（+）-Wieland-Miescher酮中，选择性地构建连续的四元手性中心。

  DOI：

  10.1016/s0040-4039(98)01284-2

文献信息

• Synthetic Studies of Zoanthamine/Norzoanthamine. Biogenetic-like One-Step Construction of the Heterocyclic Aminal Core (CDEFG Ring) from a Monocyclic Precursor.
  作者：Naotsuka HIKAGE、Hironori FURUKAWA、Ken-ichi TAKAO、Susumu KOBAYASHI

  DOI：10.1248/cpb.48.1370

  日期：——

  Biogenetic-like one-step construction of the pentacyclic aminal core of zoanthamine/norzoanthamine alkaloids was accomplished in high yield from the suitably protected monocyclic aminohydroxy diketocarboxylic acid 7 by heating in aqueous acetic acid.

  通过在乙酸水溶液中加热，由适当保护的单环氨基羟基二酮基羧酸7以高收率完成了邻氨基苯乙胺/去甲氨基苯乙胺生物碱的五环氨基环戊二烯类生物核心的一步生物构建。
• Structure–activity relationships of the truncated norzoanthamines exhibiting collagen protection toward anti-osteoporotic activity
  作者：Hironori Inoue、Kazuho Tokita、Seketsu Fukuzawa、Kazuo Tachibana

  DOI：10.1016/j.bmc.2014.04.040

  日期：2014.7

  The marine alkaloid norzoanthamine is a candidate drug for osteoporosis treatment. Due to its structural complexity, simplified analogues possessing similar biological activities are needed for further research. Recently, we found that the bisaminal unit, representing two-thirds of the original structure, is a bioactive equivalent. We synthesized three kinds of further truncated norzoanthamines and evaluated their collagen protection activities. No analog with collagen protection activity comparable to that of the bisaminal unit was found. Thus, we confirmed the importance of the bisaminal unit for the collagen protection activity. Furthermore, we found that the recognition tolerance of the substrate collagen is relatively large by comparing both enantiomers. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthetic studies of zoanthamine/norzoanthamine alkaloids: Advanced intermediate for the heterocyclic aminal core
  作者：Naotsuka Hikage、Hironori Furukawa、Ken-ichi Takao、Susumu Kobayashi

  DOI：10.1016/s0040-4039(98)01284-2

  日期：1998.8

  An advanced intermediate for the heterocyclic aminal core of zoanthaminelnorzoanthamine alkaloids was prepared in an enantio and stereoselective manner. Contiguous quaternary chiral centers were selectively constructed utilizing a stereoselective cuprate addition to the readily available (+)-Wieland-Miescher ketone.

  以对映体和立体选择性的方式制备了先进的中间体，用于制备藏菊胺基间氮杂胺生物碱的杂环氨基核。利用立体选择性铜酸盐添加到容易获得的（+）-Wieland-Miescher酮中，选择性地构建连续的四元手性中心。