(2S)-2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]propanal | 183947-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]propanal
• CAS: 183947-36-6
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: LXEJRBQQPAITKS-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]propanal 在 盐酸 、 三甲基铝 、 二甲羟胺盐酸盐 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 48.5h， 生成 (E,5R,6R)-6,7-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethylhept-3-en-2-one
  参考文献：
  名称：

  具有天然构型的calyculins四烯片段的合成

  摘要：

  四烯片段的合成2中，C 1 -C 12部分，calyculins（的1 f）曾通过使用的Stille的乙烯基碘的（C联接完成6 -C 12）单元4与腈（C 1 - C 5）单元3，然后按照巴顿法将其转化为碘乙烯官能团。

  DOI：

  10.1016/0040-4039(93)88104-q
• 作为产物：
  描述：

  diethyl (2S,3R)-2-methylmalate 在 草酰氯 、 dimethyl sulfide borane 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.25h， 生成 (2S)-2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]propanal
  参考文献：
  名称：

  Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin

  摘要：

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.

  DOI：

  10.1021/jo00084a040

文献信息

• Total synthesis of (+)-tautomycin
  作者：Satoshi Shimizu、Sei-ichi Nakamura、Masahisa Nakada、Masakatsu Shibasaki

  DOI：10.1016/0040-4020(96)00811-3

  日期：1996.10

  A convergent stereocontrolled total synthesis of (+)-tautomycin (1), a specific inhibitor of protein serine/threonine phosphatases, has been achieved through an esterification of the C1.–C7. fragment A′ 7 4 with the C1–C26 fragment B′ 7 6 by a modified Yamaguchi method and an aldol reaction of the C17–C26 fragment C 5 with the C1–C16 fragment D 6 using LDA as key steps. The fragments 5 and 6 have been

  会聚立体控制（+）的总合成- tautomycin（1），蛋白质的特异性抑制剂丝氨酸/苏氨酸磷酸酶，已经通过C的酯化实现1. -C 7片段A' 7 4与C 1 - ç 26片段B' 7 6通过改进的山口方法和C的醛醇缩合反应17 -C 26片段C 5与C 1 -C 16片段d 6使用LDA作为关键步骤。片段5和6 分别以立体声控制的方式构造。
• Synthetic studies on tautomycin synthesis of Segment B
  作者：Katsunori Tsuboi、Yoshiyasu Ichikawa、Atsushi Naganawa、Minoru Isobe、Makoto Ubukata、Kiyoshi Isono

  DOI：10.1016/s0040-4020(97)00228-7

  日期：1997.4

  The synthesis of Segment B corresponding to the C26–C17 portion of tautomycin was accomplished by coupling reaction between the epoxide (Sub-segment B-1) and the dithiane (Sub-segment B-2). The degradation product of tautomycin corresponding to the C26–C19 portion was also synthesized from Sub-segment B-1.

  对应于互变霉素C26-C17部分的B部分的合成是通过环氧化物（B-1部分）和二噻吩（B-2部分）之间的偶合反应完成的。还从子段B-1合成了对应于C26–C19部分的互变霉素的降解产物。
• Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin
  作者：Y. Guindon、C. Yoakim、V. Gorys、W. W. Ogilvie、D. Delorme、J. Renaud、G. Robinson、J.-F. Lavallee、A. Slassi

  DOI：10.1021/jo00084a040

  日期：1994.3

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.
• Synthesis of the tetraene fragment of calyculins having natural configurations
  作者：Fumiaki Yokokawa、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/0040-4039(93)88104-q

  日期：1993.10

  Synthesis of the tetraene fragment 2, the C1–C12 portion, of calyculins (1f) has been accomplished by use of the Stille coupling of the vinyl iodide (C6-C12) unit 4 with the nitrile (C1–C5) unit 3 followed by converting to the vinyl iodide function according to the Barton's procedure.

  四烯片段的合成2中，C 1 -C 12部分，calyculins（的1 f）曾通过使用的Stille的乙烯基碘的（C联接完成6 -C 12）单元4与腈（C 1 - C 5）单元3，然后按照巴顿法将其转化为碘乙烯官能团。