(3R,4S)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol | 201553-26-6

• 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,4S)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol
• 英文别名: (3R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxypent-1-en-3-ol
• CAS: 201553-26-6
• 化学式: C₄₅H₅₄O₄Si₂
• 分子量: 715.092
• InChiKey: PVPMUXRNTPPCIN-WVXCAHAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (3R,4S)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (2S,3R)-2-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-pentan-3-ol
  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-1-O-trityl-L-threitol 在 盐酸 、 4-二甲氨基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 38.5h， 生成 (3R,4S)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-1-en-3-ol
  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

文献信息

• 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.