(2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde | 241811-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde
• 英文别名: (2S,3R,5S,6S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carbaldehyde
• CAS: 241811-69-8
• 化学式: C₁₆H₃₂O₆Si
• 分子量: 348.512
• InChiKey: RUKMUEXKWHXCQB-VDERGJSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde 在 草酰氯 、 乙基溴化镁 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 (2S,3R,5S,6S)-2-(1'-hydroxy-prop-2'-yn-1'-yl)-3-vinyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane
  参考文献：
  名称：

  Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside

  摘要：

  The synthesis of carbasugar analogue tetracetate 4a-carba-D-xylofuranoside (1) was reported. The new route involved the conversion of D-(-)-tartatic acid into an enyne compound, which was then cyclized via a key ring-closing enyne metathesis to form the key intermediate 1-vinyl cyclopentene 9, which was then stereoselectively converted to our target. The absolute configuration of the en ne was determined by modified Mosher's method, while that of tetracetate 4a-carba-D-xylofuranoside by ROSEY spectroscopy and gamma-gauche effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.139
• 作为产物：
  描述：

  二甲基(2S,3S,5S,6S)-5,6-二甲氧基-5,6-二甲基-1,4-二恶烷-2,3-二羧酸酯 在 lithium aluminium tetrahydride 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 (2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde
  参考文献：
  名称：

  antascomicin B 的全合成。

  摘要：

  DOI：

  10.1002/anie.200500174

文献信息

• A Clean Conversion of Aldehydes to Nitriles Using a Solid-Supported Hydrazine
  作者：Ian R. Baxendale、Steven V. Ley、Helen F. Sneddon

  DOI：10.1055/s-2002-25333

  日期：——

  A polymer-supported hydrazine reagent has been ap- plied to the conversion of a range of aldehydes to nitriles, providing a clean and efficient route to more diverse building blocks for com- binatorial chemistry programmes.

  聚合物负载的肼试剂已被应用于将一系列醛类转化为腈类，为组合化学程序提供了一条清洁、有效的途径，以构建更加多样化的构建模块。
• Barlow, Jaqueline S.; Dixon, Darren J.; Foster, Alison C., Journal of the Chemical Society. Perkin transactions I, 1999, # 12, p. 1627 - 1629
  作者：Barlow, Jaqueline S.、Dixon, Darren J.、Foster, Alison C.、Ley, Steven V.、Reynolds, Dominic J.

  DOI：——

  日期：——
• Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside
  作者：Zhi Jie Xue、Ping Chen、Shu Ying Peng、Yuan Chao Li

  DOI：10.1016/j.tet.2005.09.139

  日期：2006.1

  The synthesis of carbasugar analogue tetracetate 4a-carba-D-xylofuranoside (1) was reported. The new route involved the conversion of D-(-)-tartatic acid into an enyne compound, which was then cyclized via a key ring-closing enyne metathesis to form the key intermediate 1-vinyl cyclopentene 9, which was then stereoselectively converted to our target. The absolute configuration of the en ne was determined by modified Mosher's method, while that of tetracetate 4a-carba-D-xylofuranoside by ROSEY spectroscopy and gamma-gauche effect. (c) 2005 Elsevier Ltd. All rights reserved.
• Total Synthesis of Antascomicin B
  作者：Dominic E. A. Brittain、Charlotte M. Griffiths‐Jones、Michael R. Linder、Martin D. Smith、Catherine McCusker、Jaqueline S. Barlow、Ryo Akiyama、Kosuke Yasuda、Steven V. Ley

  DOI：10.1002/anie.200500174

  日期：2005.4.29