Acetic acid 2-tributylstannanyl-penta-2,3-dienyl ester | 171011-57-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid 2-tributylstannanyl-penta-2,3-dienyl ester
• CAS: 171011-57-7
• 化学式: C₁₉H₃₆O₂Sn
• 分子量: 415.204
• InChiKey: UDYJIEWLBDSDIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-tributylstannanyl-penta-2,3-dienyl ester 在 camphor-10-sulfonic acid 、 丁基三氯化锡 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 Acetic acid (S)-4-[(2R,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pent-2-ynyl ester
  参考文献：
  名称：

  通过将非外消旋的烯丙基锡烷醛加到醛上的S（E）2'加成合成Discodermolide亚基。

  摘要：

  从（S）-3-[（叔丁基二甲基甲硅烷基）氧基] -2-甲基丙醛（（S）-1）和对映体富集的烯丙斯坦酮（P）制备了免疫抑制剂二糖单核苷酸的三个亚基15、29和34 -2a，（P）-2b和（P）-31。到达15的途径涉及BF（3）促进将金刚烷（P）-2a添加到醛（S）-1中，从而以97％的产率提供了顺式，顺式-同炔丙基醇加合物3。衍生的对甲氧基亚苄基乙缩醛5用Red-Al处理，以实现新戊酸酯的裂解和双键的还原，从而导致（E）-烯丙基醇6。急剧的环氧化和随后的Me（2）CuCNLi（2）添加得到顺式，顺式，顺式，反立体五醇，二醇8。保护仲醇并氧化伯，得到醛12，将其用α-溴烯丙基硅烷13和CrCl（2）处理，然后用NaH消除二烯15。采用类似的步骤制备醛29。在这种情况下，通过将Sn-1生成的烯丙基铟试剂处理，将其转化为反正同炔丙醇20。原位于烯丙基锡烷（P）-2b和InBr（3）。按照上述顺序

  DOI：

  10.1021/jo971900+

文献信息

• Total Synthesis and Structure Confirmation of Leptofuranin D
  作者：James A. Marshall、Gregory M. Schaaf

  DOI：10.1021/jo0348930

  日期：2003.9.1

  hydrogenolysis of the derived bromide 19. Hydrostannation of the terminal alkyne converted 21 to 22, which was then treated with iodine to afford the vinyl iodide 23. The dihydropyranone precursor 40 was prepared by addition of allenystannane 29 to aldehyde 27. Partial hydrogenation of the derived propargylic alcohol then protection as the TBS ether afforded the (Z)-olefin 34. Further homologation was effected

  描述了呋喃呋喃丁酮D的收敛的全合成。通过将衍生自甲磺酸酯12的手性烯丙基锌试剂添加到手性醛11中，组装线性聚酮化合物C12-C24片段。将加合物13定向加氢氢化，然后进行碘裂解和Sonogashira偶联，生成烯炔16，将其转化为苯乙炔。通过衍生的溴化物19的氢解，将甲基取代的烯基20甲基化。将末端炔烃转化为21到22的炔烃进行氢化，然后用碘进行处理，得到乙烯基碘23。二氢吡喃酮前体40是通过将烯丙基锡烷29添加到醛中而制得的27.将衍生的炔丙醇部分氢化，然后将其作为TBS醚进行保护，得到（Z）-烯烃34。通过醛36与衍生自溴化phospho37的叶立德的维特希缩合反应实现进一步的同源性。38的伯TES醚的选择性脱保护，然后将醇39转化为碘40，完成了C1-C11链段的合成。由碘化物40制备的硼酸酯41与乙烯基碘化物23的Suzuki偶联生成二烯42，具有上呋喃丹D的完整碳骨架。通过氧化未
• Synthesis of a Bistetrahydrofuran C17−C32 Fragment of the Polyether Antibiotic Ionomycin
  作者：James A. Marshall、Ann M. Mikowski

  DOI：10.1021/ol061826u

  日期：2006.9

  A Zn-initiated triepoxide cascade cyclization reaction was employed for the synthesis of the bistetrahydrofuran core segment of the polyether ionophore antibiotic ionomycin.

  锌引发的三环氧化物级联环化反应用于合成聚醚离子载体抗生素离子霉素的双四氢呋喃核心链段。
• Comparative Studies on the Synthesis of an <i>anti,syn</i> Stereotriad with Chiral Allenylstannane and Allenylindium Reagents
  作者：James A. Marshall、Michael R. Palovich

  DOI：10.1021/jo970650u

  日期：1997.8.1

  Addition of the chloroallenylstannane derived from the Bu3Sn allene (S)-2 and SnCl4 to nonracemic alpha-methyl-beta-oxygenated aldehyde 1a afforded mixtures of anti,syn and anti,anti adducts 3a and 3b. When InCl3 was employed in the transmetalation of allenylstannane (S)-2, a mixture of adducts 3a and ent-3b was produced. Experiments with the beta-ODPS aldehydes 1b and 5 showed that InBr3 and InI3 yield a transient InXn species from allenylstannane (S)-2 with mainly retention of configuration. In contrast, transmetalation of (S)-2 with SnCl4 or BuSnCl3 affords an intermediate allenyl species of inverted configuration. The (S)-2/BuSnCl3 reagent showed high enantio-and diastereoselectivity in addition to aldehydes 1a, 1b, and 5. The (S)-2/InBr3 or InI3 reagent, while somewhat less selective, afforded enantiomeric or diastereomeric adducts.
• Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents
  作者：James A. Marshall、Jolyon F. Perkins、Mark A. Wolf

  DOI：10.1021/jo00122a041

  日期：1995.9

  The stannanes (S)-1a, (R)-1b, and (S)-1c add to (S)- and (R)-2-methyl-3-(benzyloxy)propanal ((S)-2 and (R)-2) to afford the syn,syn (BF3 . OEt(2) promotion), syn,anti (MgBr2 . OEt(2) promotion), anti,anti (SnCl4-derived reagent in CH2Cl2), and anti,syn (SnCl4-derived reagent in hexane) stereotriad adducts 3, 4, 6, and 7.
• Synthesis of Stereopentad Subunits of Zincophorin and Rifamycin-S through Use of Chiral Allenyltin Reagents
  作者：James A. Marshall、Michael R. Palovich

  DOI：10.1021/jo980137w

  日期：1998.5.1

  The anti,anti adduct 3, from addition of the allenic stannane (P)-2 to the alpha-methyl-beta-OBn aldehyde (S)-1 promoted by SnCl4, was converted to the stereopentad 6 by a sequence involving reduction to the (E)-allylic alcohol with Red-Al, Sharpless asymmetric epoxidation, and addition of the higher-order methyl cyanocuprate to the derived epoxide 5. Stereopentad 6 was converted to the acetonide acetal 15, an intermediate in Danishefsky's synthesis of zincophorin. By a similar sequence, adduct ent-4 was converted, via diol 19, to stereopentad 22, an intermediate in Kishi's synthesis of rifamycin-S. An alternative route to diol 19 was achieved from the MOM-protected derivative 28 of epoxy diol 18.