(5'R)-5'-{(1R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-{[tert-butyl(diphenyl)silyl]oxy}-8-[(para-methoxybenzyl)oxy]oct-2-ynyl}dihydrofuran-2'(3H)-one | 1001671-39-1

• 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: (5'R)-5'-{(1R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-{[tert-butyl(diphenyl)silyl]oxy}-8-[(para-methoxybenzyl)oxy]oct-2-ynyl}dihydrofuran-2'(3H)-one
• CAS: 1001671-39-1
• 化学式: C₄₂H₅₈O₆Si₂
• 分子量: 715.09
• InChiKey: RFLCGNIKFBBSMN-LDOMGJARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5'R)-5'-{(1R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-{[tert-butyl(diphenyl)silyl]oxy}-8-[(para-methoxybenzyl)oxy]oct-2-ynyl}dihydrofuran-2'(3H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (4R,5R,8R)-8-{[tert-butyl(dimethyl)silyl]oxy}-5-{[tert-butyl(diphenyl)silyl]oxy}-12-[(para-methoxybenzyl)oxy]dodec-6-yne-1,4-diol 、 (4R,5R,8R)-8-{[tert-butyl(dimethyl)silyl]oxy}-12-[(para-methoxybenzyl)oxy]dodec-6-yne-1,4,5-triol
  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：

  (5'R)-5'-{(1R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-hydroxy-8-[(para-methoxybenzyl)oxy]oct-2-ynyl}dihydrofuran-2'(3H)-one 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以2.19 g的产率得到(5'R)-5'-{(1R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-{[tert-butyl(diphenyl)silyl]oxy}-8-[(para-methoxybenzyl)oxy]oct-2-ynyl}dihydrofuran-2'(3H)-one
  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