(2R,3R,4R,5R,6E,8S,9Z)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-4-[(4-methoxyphenyl)methoxymethyl]-2,6,8-trimethyl-3-triethylsilyloxyundeca-6,9-dien-5-ol | 1352952-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3R,4R,5R,6E,8S,9Z)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-4-[(4-methoxyphenyl)methoxymethyl]-2,6,8-trimethyl-3-triethylsilyloxyundeca-6,9-dien-5-ol
• CAS: 1352952-91-0
• 化学式: C₅₀H₆₈O₇Si
• 分子量: 809.171
• InChiKey: RVSMRIDHMIGEKD-XTJUUHSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  58
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3R)-1,1-dibromo-3-methyl-4-(tert-butyldimethylsilyloxy)-1-butene 在 正丁基锂 、 叔丁基锂 、 六正丁基二锡 、 copper(l) cyanide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (2R,3R,4R,5S,6E,8S,9Z)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-4-[(4-methoxyphenyl)methoxymethyl]-2,6,8-trimethyl-3-triethylsilyloxyundeca-6,9-dien-5-ol 、 (2R,3R,4R,5R,6E,8S,9Z)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-4-[(4-methoxyphenyl)methoxymethyl]-2,6,8-trimethyl-3-triethylsilyloxyundeca-6,9-dien-5-ol
  参考文献：
  名称：

  Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide

  摘要：

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.024

文献信息

• Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide
  作者：Michael E. Jung、Dongwon Yoo

  DOI：10.1016/j.tet.2011.10.024

  日期：2011.12

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.