(R)-1-((4R,5S)-5-((S)-1-(benzylamino)-but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyl-dimethylsilyloxy)ethanol | 1233851-78-9

• 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: (R)-1-((4R,5S)-5-((S)-1-(benzylamino)-but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyl-dimethylsilyloxy)ethanol
• 英文别名: (1R)-1-[(4R,5S)-5-[(1S)-1-(benzylamino)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[tert-butyl(dimethyl)silyl]oxyethanol
• CAS: 1233851-78-9
• 化学式: C₂₄H₄₁NO₄Si
• 分子量: 435.679
• InChiKey: NBSFWYNPBUQIQT-LNRXMEIDSA-N

物化性质

• 沸点：
  488.2±45.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-((4R,5S)-5-((S)-1-(benzylamino)-but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyl-dimethylsilyloxy)ethanol 在 咪唑 、 sodium tetrahydroborate 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 cerium(III) chloride heptahydrate 、 dimethyl sulfide borane 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 14.67h， 生成 benzyl benzyl((S)-1-((4S,5S)-5-((R)-3,3-diethyl-8,8,9,9-tetramethyl-4,7-dioxa-3,8-disiladecan-5-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(hydroxymethyl)but-3-enyl)carbamate
  参考文献：
  名称：

  A new stereoselective approach to aminocyclohexitols using RCM

  摘要：

  A new stereoselective approach for the synthesis of carbamannopyranosylamine and epi-valiolamine by using stereoselective allylation on lactamine and RCM from D-ribose has been described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.009
• 作为产物：
  描述：

  5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 在 sodium sulfate 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-1-((4R,5S)-5-((S)-1-(benzylamino)-but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyl-dimethylsilyloxy)ethanol
  参考文献：
  名称：

  A new stereoselective approach to aminocyclohexitols using RCM

  摘要：

  A new stereoselective approach for the synthesis of carbamannopyranosylamine and epi-valiolamine by using stereoselective allylation on lactamine and RCM from D-ribose has been described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.009

文献信息

• A new stereoselective approach for N-benzyl amino(hydroxymethyl)cyclopentitols using RCM
  作者：J. Prasada Rao、B. Venkateswara Rao、J. Lakshmi swarnalatha

  DOI：10.1016/j.tetlet.2010.04.011

  日期：2010.6

  A new stereoselective approach for the synthesis of N-benzyl amino(hydroxymethyl)cyclopentitols by using stereoselective allylation on lactamine and RCM from d-ribose has been described and the glycosidase inhibitory activities of these amino cyclopentitols have been studied.

  已经描述了一种新的立体选择性方法，该方法通过在D-核糖上对乳糖胺和RCM进行立体选择性烯丙基化来合成N-苄基氨基（羟甲基）环戊糖醇，并且已经研究了这些氨基环戊糖醇的糖苷酶抑制活性。
• A Divergent and Stereoselective Approach for the Syntheses of Some Polyhydroxylated Indolizidine and Pyrrolizidine Iminosugars
  作者：Anugula Rajender、Jalagam Prasada Rao、Batchu Venkateswara Rao

  DOI：10.1002/ejoc.201201342

  日期：2013.3

  A common, divergent, and efficient approach to the syntheses of (+)-steviamine (9), (–)-1-deoxy-8a-epi-castanospermine (10), (+)-trihydroxyindolizidine (11), (+)-3,7a-di-epi-hyacinthacine A1 (12), and (–)-2-epi-lentiginosine (4) was achieved by starting from D-ribose-derived intermediate 13. The key steps involved in these syntheses are a highly diasteroselective Grignard addition to a ribosylimine

  (+)-steviamine (9), (–)-1-deoxy-8a-epi-castanospermine (10), (+)-trihydroxyindolizidine (11), (+) -3,7a-di-epi-hyacinthacine A1 (12) 和 (-)-2-epi-lentiginosine (4) 是从 D-核糖衍生的中间体 13 开始获得的。这些合成中涉及的关键步骤是核糖亚胺的高度非对映选择性格氏加成、一锅立体选择性分子内还原胺化、甲硅烷基醚的选择性脱保护和闭环复分解 (RCM) 反应。
• A new stereoselective approach to aminocyclohexitols using RCM
  作者：Anugula Rajender、Jalagam Prasada Rao、Batchu Venkateswara Rao

  DOI：10.1016/j.tetasy.2011.07.009

  日期：2011.6

  A new stereoselective approach for the synthesis of carbamannopyranosylamine and epi-valiolamine by using stereoselective allylation on lactamine and RCM from D-ribose has been described. (C) 2011 Elsevier Ltd. All rights reserved.