(6S)-6-((4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxyhex-1-en-3-ol | 1032879-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6S)-6-((4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxyhex-1-en-3-ol
• CAS: 1032879-87-0
• 化学式: C₂₉H₄₂O₅Si
• 分子量: 498.735
• InChiKey: AQWWXCQIMBWHLX-ZYDVDNKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (6S)-6-((4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxyhex-1-en-3-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以53%的产率得到
  参考文献：
  名称：

  Synthesis of the C1−C23 Fragment of Spirastrellolide A

  摘要：

  Synthesis of the C1-C23 fragment in spirastrellolide A is described, featuring a cyclic acetal-tethered RCM for stereoselective constructions of spiroketal, and a 1,3-anti aldol involving methyl ketone enolate and Mukaiyama conditions.

  DOI：

  10.1021/ol8008057
• 作为产物：
  描述：

  (4S,5S)-2,2-二甲基-1,3-二氧戊环-4,5-二甲醇 在 (-)-B-methoxydiisopinocamphenylborane 、 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (6S)-6-((4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxyhex-1-en-3-ol
  参考文献：
  名称：

  ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL

  摘要：

  We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered ring-closing metathesis [RCM] method that was developed in our lab for de novo synthesis of spiroketals. Constructing the entire Southern Half of the macrocycle would require 1,3-anti-Mukaiyama aldol addition for connecting A-ring and BC-ring specifically at C10 and C11, thereby culminating a 17-step approach for the Southern Macrocyclic Half linearly from (+)-2,3-(O)-iso-propylidene-L-threitol. Also discussed here is the possibility of pursuing a more convergent approach toward the assembly of the Southern Half through first connecting A-ring and C-ring via acetal formation that would first link together the free C13-OH with C17 at the spiro-BC-ring junction. An ensuing application of our cyclic acetal-tethered RCM strategy to close B-ring would adopt this cyclic acetal intermediate.

  DOI：

  10.3987/com-12-s(n)54