(5R,6R,7E,9R)-9-{[tert-butyl(dimethyl)silyl]oxy}-6-{[tert-butyl(diphenyl)silyl]oxy}-13-[(para-methoxybenzyl)oxy]-5-(methoxymethoxy)tridec-7-en-1yne | 1001671-49-3

• 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: (5R,6R,7E,9R)-9-{[tert-butyl(dimethyl)silyl]oxy}-6-{[tert-butyl(diphenyl)silyl]oxy}-13-[(para-methoxybenzyl)oxy]-5-(methoxymethoxy)tridec-7-en-1yne
• 英文别名: tert-butyl-[(E,5R,6R,9R)-9-[tert-butyl(dimethyl)silyl]oxy-5-(methoxymethoxy)-13-[(4-methoxyphenyl)methoxy]tridec-7-en-1-yn-6-yl]oxy-diphenylsilane
• CAS: 1001671-49-3
• 化学式: C₄₅H₆₆O₆Si₂
• 分子量: 759.186
• InChiKey: PDRYSKLFOWMTHH-UNZLLHSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  53
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5R,6R,7E,9R)-9-{[tert-butyl(dimethyl)silyl]oxy}-6-{[tert-butyl(diphenyl)silyl]oxy}-13-[(para-methoxybenzyl)oxy]-5-(methoxymethoxy)tridec-7-en-1yne 、 methyl (2E,4R,5R,7E)-8-iodo-2,4,7-trimethyl-5-[(triethylsilyl)oxy]-2,7-octadienoate 在 bis-triphenylphosphine-palladium(II) chloride 、 tris(dibenzylideneacetone)dipalladium (0) 三正丁基氢锡 、 三苯胂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 以78%的产率得到methyl (2E,4R,5R,7E,9E,13R,14R,15E,17R)-17-{[tert-butyl(dimethyl)silyl]oxy}-14-{[tert-butyl(diphenyl)silyl]oxy}-21-[(para-methoxybenzyl)oxy]-13-methoxymethoxy-2,4,7-trimethyl-5-[(triethylsilyl)oxy]henicosa-2,7,9,15-tetraenoate
  参考文献：
  名称：

  A concise route to the C3–C23 fragment of the macrolide palmerolide A

  摘要：

  A concise route to the C3-C23 part of the macrolide palmerolide A was developed. This part features the 7,10,11-trihydroxy sector containing the 8E-double bond as well as the 14,16-diene subunit. The stereocenter at C-7 originated from a Noyori reduction on alkynone 8. The substrate 16 containing an enyne was obtained via a Claisen rearrangement. The vicinal diol at C10,C11 was created by a Sharpless asymmetric dihydroxylation. After selective protecting group manipulations the propargylic alcohol was reduced with Red-Al to the E-alkylic alcohol 26. The conjugated diene in the fragment 40 resulted from a Stille cross-coupling reaction between the vinylstarmane derived from alkyne 30 and the vinyl iodide 39. The latter could conveniently be prepared by an aldol/Wittig strategy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.028
• 作为产物：
  描述：

  (5R,6E,8R,9R)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-[(para-methoxybenzyl)oxy]-9-(methoxymethoxy)tridec-6-en-12-yn-5-ol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以93%的产率得到(5R,6R,7E,9R)-9-{[tert-butyl(dimethyl)silyl]oxy}-6-{[tert-butyl(diphenyl)silyl]oxy}-13-[(para-methoxybenzyl)oxy]-5-(methoxymethoxy)tridec-7-en-1yne
  参考文献：
  名称：

  A concise route to the C3–C23 fragment of the macrolide palmerolide A

  摘要：

  A concise route to the C3-C23 part of the macrolide palmerolide A was developed. This part features the 7,10,11-trihydroxy sector containing the 8E-double bond as well as the 14,16-diene subunit. The stereocenter at C-7 originated from a Noyori reduction on alkynone 8. The substrate 16 containing an enyne was obtained via a Claisen rearrangement. The vicinal diol at C10,C11 was created by a Sharpless asymmetric dihydroxylation. After selective protecting group manipulations the propargylic alcohol was reduced with Red-Al to the E-alkylic alcohol 26. The conjugated diene in the fragment 40 resulted from a Stille cross-coupling reaction between the vinylstarmane derived from alkyne 30 and the vinyl iodide 39. The latter could conveniently be prepared by an aldol/Wittig strategy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.028

文献信息

• A concise route to the C3–C23 fragment of the macrolide palmerolide A
  作者：Julia Jägel、Anke Schmauder、Michael Binanzer、Martin E. Maier

  DOI：10.1016/j.tet.2007.10.028

  日期：2007.12

  A concise route to the C3-C23 part of the macrolide palmerolide A was developed. This part features the 7,10,11-trihydroxy sector containing the 8E-double bond as well as the 14,16-diene subunit. The stereocenter at C-7 originated from a Noyori reduction on alkynone 8. The substrate 16 containing an enyne was obtained via a Claisen rearrangement. The vicinal diol at C10,C11 was created by a Sharpless asymmetric dihydroxylation. After selective protecting group manipulations the propargylic alcohol was reduced with Red-Al to the E-alkylic alcohol 26. The conjugated diene in the fragment 40 resulted from a Stille cross-coupling reaction between the vinylstarmane derived from alkyne 30 and the vinyl iodide 39. The latter could conveniently be prepared by an aldol/Wittig strategy. (c) 2007 Elsevier Ltd. All rights reserved.