(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol | 171622-74-5

• 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: (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol
• 英文别名: (2R,3R)-4-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-4-pentene；(2R,3R)-4-[tert-butyl(dimethyl)silyl]oxy-2,3-bis(phenylmethoxy)butan-1-ol
• CAS: 171622-74-5
• 化学式: C₂₄H₃₆O₄Si
• 分子量: 416.633
• InChiKey: VEPNZTJBBXPZOO-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 (3R,4R)-3,4-dibenzyloxy-5-tert-butyldimethylsilyloxypent-1-yne
  参考文献：
  名称：

  校正“二炔的金（I）催化多米诺环化反应，以合成功能化的环己烯酮衍生物。（-）-Gabosine H和（-）-6- Epi -Gabosine H的全合成”

  摘要：

  （ - ） - gabosine H（错误的对映异构体5），（ - ） -外延-gabosine H（EPI -5）和中间体6 - 10，图11A，b，和12 - 22在摘要垂落，目录，以及方案2-6。提供了这些化合物的正确结构图。显示了已更正的摘要和目录图形：已更正的方案2–6：在参考文献4中，我们无意中忽略了相关的评论：（c​​）Marion，N .; Nolan，SP Angew。化学 诠释 埃德 2007年，46，2750–2752。有关结构不正确的错误不会影响支持信息的实验部分提供的任何报告的产量，数据或信息的有效性。此外，来文的结果和结论也仍然有效。不便之处，敬请原谅。可在ACS出版物网站上免费获得支持信息：DOI：10.1021 / acs.orglett.6b02509。 修订后的支持信息（结构更正）（PDF）经修订的具有正确结构的支持信息（PDF）其他出版物尚未引用此文章

  DOI：

  10.1021/acs.orglett.6b02509
• 作为产物：
  描述：

  S-tert-butyl 2-(benzyloxy)ethanethioate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 N,N-二甲基乙醇胺 、 dicobalt octacarbonyl 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 三氯硅烷 、 四丁基碘化铵 、 sodium hydride 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol
  参考文献：
  名称：

  有机合成中钴络合的丙烯腈：苯甲酰胺E的高度立体选择性全合成

  摘要：

  钴络合的4-甲基戊-2-炔2与O-甲硅烷基烯酮O，S-缩醛3的高度立体选择性羟醛反应提供了顺式羟醛产物，随后通过光学拆分将其转化为（+）-联酰胺E和第二个非对映选择性羟醛反应是关键步骤。

  DOI：

  10.1016/0040-4039(94)85036-4

文献信息

• Total Syntheses of (+)-Secosyrins 1 and 2 and (+)-Syributins 1 and 2
  作者：Chisato Mukai、Sameh M. Moharram、Satoru Azukizawa、Miyoji Hanaoka

  DOI：10.1021/jo9711089

  日期：1997.11.1

  First total syntheses of (+)-secosyrins 1 and 2 and total syntheses of (+)-syributins 1 and 2 are described. The two chiral centers of diisopropyl tartrate were incorporated into target natural products. Stereoselective construction of the spiro skeleton of secosyrins could be realized by taking advantage of an alkyne-cobalt complex. The synthesis of these compounds established their relative and absolute

  首先描述（+）-丝球菌素1和2的总合成，以及（+）-丝氨酸酪蛋白1和2的总合成。将酒石酸二异丙酯的两个手性中心并入目标天然产物中。可以通过利用炔-钴配合物来实现立体定位的椰油香豆素螺旋骨架的立体选择性构建。这些化合物的合成明确地建立了它们的相对和绝对立体化学。
• Highly stereocontrolled total synthesis of (+)-bengamide E
  作者：Chisato Mukai、Sameh M. Moharram、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1039/p19950002849

  日期：——

  Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23. A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence oi tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.
• An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1
  作者：Chisato Mukai、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1021/jo00123a030

  日期：1995.9

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.
• Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring-Closing Metathesis Reactions
  作者：Jung-Nyoung Heo、Glenn C. Micalizio、William R. Roush

  DOI：10.1021/ol034347t

  日期：2003.5.1

  [GRAPHICS]Highly enantioenriched cyclic allylsilanes are prepared via stereoselective gamma-silylallylboration reactions of beta- or gamma-unsaturated aldehydes followed by ring-closing metathesis.
• Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization
  作者：Gaëlle Fourrière、Eric Leclerc、Jean-Charles Quirion、Xavier Pannecoucke

  DOI：10.1016/j.jfluchem.2011.02.015

  日期：2012.2

  The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5-methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one. (C) 2011 Elsevier B.V. All rights reserved.