(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al | 1274953-67-1

• 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: (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al
• 英文别名: (3S,5S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxybenzyloxy)-heptan-1-al；(3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-[(4-methoxyphenyl)methoxy]heptanal
• CAS: 1274953-67-1
• 化学式: C₂₇H₅₀O₅Si₂
• 分子量: 510.862
• InChiKey: FLJRHNOIUZKNTM-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Enantio- and Diastereoselective Synthesis of (E)-1,5-syn-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin

  摘要：

  A highly stereoselective synthesis of (E)-1,5-syn-diols 6 Is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 In 72-98% yields with > 95% ee and > 20:1 dr. Application of this method to the synthesis of the tetraflbricin C(23)-C(40) fragment 19 is described.

  DOI：

  10.1021/ol2003836
• 作为产物：
  描述：

  (E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al 在 咪唑 、 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 sodium periodate 、 四氧化锇 、 D-(-)-酒石酸二乙酯 、 红铝 、 (-)-B-methoxydiisopinocampheylborane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 54.0h， 生成 (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al
  参考文献：
  名称：

  Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: application to the synthesis of the C(23)–C(40) fragment of tetrafibricin

  摘要：

  Interest in the synthesis of the C(23) C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23) C(40) fragment 2 of tetrafibricin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.008

文献信息

• Diisopinocampheylborane-Mediated Reductive Aldol Reactions: Highly Enantio- and Diastereoselective Synthesis of<i>syn</i>Aldols from<i>N</i>-Acryloylmorpholine
  作者：Philippe Nuhant、Christophe Allais、William R. Roush

  DOI：10.1002/anie.201302535

  日期：2013.8.12

  inexpensive and straightforward synthesis of syn‐propionamide aldols, formation of the Z enolborinate by the hydroboration of 4‐acryloylmorpholine with diisopinocampheylborane ((Ipc)2BH) was followed by aldol reactions with achiral and chiral aldehydes to provide syn‐α‐methyl‐β‐hydroxymorpholinecarboxamides with excellent enantio‐ and diastereoselectivity (see scheme; R=alkyl, alkenyl, aryl, heteroaryl).

  削减成本，切削角：在一种廉价和简单的合成顺式-丙酰胺醛醇，在形成的Ž由4-丙烯酰基吗啉与diisopinocampheylborane（（IPC）的硼氢化enolborinate 2 BH），随后用非手性和手性醛羟醛缩合反应提供具有优异对映选择性和非对映选择性的顺-α-甲基-β-羟基吗啉甲酰胺（参见方案；R=烷基、烯基、芳基、杂芳基）。
• (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of <i>Anti</i>-Aldols
  作者：Christophe Allais、Philippe Nuhant、William R. Roush

  DOI：10.1021/ol401679g

  日期：2013.8.2

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.
• 10.15227/orgsyn.92.0038
  作者：Abbott, Jason R.、Allais, Christophe、Roush, William R.

  DOI：10.15227/orgsyn.92.0038

  日期：——