(3R)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-one | 183888-69-9

• 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: (3R)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-one
• 英文别名: (3S)-1,4-bis[[tert-butyl(diphenyl)silyl]oxy]-3-phenylmethoxybutan-2-one
• CAS: 183888-69-9
• 化学式: C₄₃H₅₀O₄Si₂
• 分子量: 687.039
• InChiKey: LHDQSXGUBDEJPU-RWYGWLOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (3R)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-one 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 (2R,3S)-1,3,4-tri-O-benzyl-2-ethylbutane-1,2,3,4-tetraol
  参考文献：
  名称：

  Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives

  摘要：

  We have investigated a number of nucleophillic additions to L-erythrulose derivatives (4-12) bearing protective O-silyl, O-benzyl, and O-trityl groups in various relative positions. The results are discussed in the frame of chelated vs nonchelated transition states with additional support of previously published theoretical calculations. Sound evidence appears to exist for the formation of alpha-chelates as the key intermediates in nucleophillic additions to these alpha,beta-dioxygenated ketones. Since such evidence is still lacking in the case of beta-chelates, proposals of their intermediacy have been relegated in favor of the more solid Felkin-Anh model, which predicts the same stereochemical result. The behavior of these highly functionalized ketones does not always match that of structurally similar aldehydes.

  DOI：

  10.1021/jo9716744
• 作为产物：
  描述：

  2-O-benzyl-L-threitol 在 吡啶 、 4-二甲氨基吡啶 、 molecular sieve 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (3R)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-one
  参考文献：
  名称：

  分子内亚烷基卡宾反应的研究；杂环核苷碱基的方法

  摘要：

  描述了对亚烷基卡宾分子内环化的应用的一系列研究。由1，4-二（叔丁基二甲基甲硅烷基氧基）-3-苄氧基丁烷-2-一生成的卡宾向苄基位置的插入反应以良好的收率和3.6∶1的非对映选择性进行。1,4-二（叔丁基二甲基甲硅烷氧基）-3-甲氧基甲基丁烷-2-一的相应插入过程产生了一种产物混合物，其中包括一种由于卡宾被甲硅烷氧基的氧原子竞争性捕获而产生的产物。

  DOI：

  10.1016/s0040-4020(03)00692-6

文献信息

• Marco, J. Alberto; Carda, Miguel; Gonzalez, Florenci, Liebigs Annalen, 1996, # 11, p. 1801 - 1810
  作者：Marco, J. Alberto、Carda, Miguel、Gonzalez, Florenci、Rodriguez, Santiago、Murga, Juan

  DOI：——

  日期：——
• Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives
  作者：J. Alberto Marco、Miguel Carda、Florenci González、Santiago Rodríguez、Encarna Castillo、Juan Murga

  DOI：10.1021/jo9716744

  日期：1998.2.1

  We have investigated a number of nucleophillic additions to L-erythrulose derivatives (4-12) bearing protective O-silyl, O-benzyl, and O-trityl groups in various relative positions. The results are discussed in the frame of chelated vs nonchelated transition states with additional support of previously published theoretical calculations. Sound evidence appears to exist for the formation of alpha-chelates as the key intermediates in nucleophillic additions to these alpha,beta-dioxygenated ketones. Since such evidence is still lacking in the case of beta-chelates, proposals of their intermediacy have been relegated in favor of the more solid Felkin-Anh model, which predicts the same stereochemical result. The behavior of these highly functionalized ketones does not always match that of structurally similar aldehydes.
• Studies of intramolecular alkylidene carbene reactions; an approach to heterocyclic nucleoside bases
  作者：Gerard Hobley、Keith Stuttle、Martin Wills

  DOI：10.1016/s0040-4020(03)00692-6

  日期：2003.6

  A series of investigations into the applications of intramolecular cyclisations of alkylidene carbenes are described. The insertion reaction of the carbene generated from 1,4-di(tert-butyldimethylsilyloxy)-3-benzyloxy-butane-2-one to the benzylic position proceeded in good yield and a diastereoselectivity of 3.6:1. The corresponding insertion process of 1,4-di(tert-butyldimethylsilyloxy)-3-methylo

  描述了对亚烷基卡宾分子内环化的应用的一系列研究。由1，4-二（叔丁基二甲基甲硅烷基氧基）-3-苄氧基丁烷-2-一生成的卡宾向苄基位置的插入反应以良好的收率和3.6∶1的非对映选择性进行。1,4-二（叔丁基二甲基甲硅烷氧基）-3-甲氧基甲基丁烷-2-一的相应插入过程产生了一种产物混合物，其中包括一种由于卡宾被甲硅烷氧基的氧原子竞争性捕获而产生的产物。