(2R,4R,3S)-3-hydroxy-2,4-dimethylbutyrolactone | 98512-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2R,4R,3S)-3-hydroxy-2,4-dimethylbutyrolactone
• 英文别名: (2R,3R,4S)-2-methyl-3,4-dihydroxypentanoic acid 1,4-lactone；(3R,4R,5S)-4-hydroxy-3,5-dimethyloxolan-2-one
• CAS: 98512-77-7
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: BSTCHFGEIXFVRN-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,4R,5R,6S)-2-[tert-butyl(dimethyl)silyl]oxy-6-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-4-methylheptan-3-one 在 sodium periodate 、 氢氟酸 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 60.0h， 生成 (2R,4R,3S)-3-hydroxy-2,4-dimethylbutyrolactone
  参考文献：
  名称：

  手性Z-烯醇钛与手性α-甲硅烷氧基醛的反应。NFX-2和抗霉素的合成

  摘要：

  钛介导的1和（S）-2-叔丁基二苯基甲硅烷氧基醛（匹配对）的醇醛缩合反应可提供出色的收率和绝对的立体化学控制的合成Felkin非对映异构体。确定链长不会影响钛醇醛缩合反应的收率，我们已经能够实现NFX-2和抗霉素的短，高收率和对映选择性合成。

  DOI：

  10.1016/s0040-4039(99)00987-9

文献信息

• Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters
  作者：Cesare Gennari、Anna Bernardi、Silvia Cardani、Carlo Scolastico

  DOI：10.1016/0040-4020(84)85086-3

  日期：1984.1

  dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products. The thioester additions to chiral aldehydes were studied. Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used. The aldol products were transformed to known compounds for correlation

  进行了详细的研究，将硫代丙酸苯基酯与亚乙基氯硼酸酯（ECB）和二异丙基乙胺（DPEA）进行烯醇化，随后对这些烯醇化物进行醇醛缩合反应。已发现衍生自硫酯的烯氧基二烷氧基硼烷是立体收敛的：Z和E的烯醇盐均生成顺式醇醛缩合产物。研究了手性醛中硫代酯的添加。内部选择性（syn）通常很高，而相对的立体选择性则根据所使用的特定醛的不同，从差到好。将醛醇缩合产物转化为已知化合物以进行相关。
• Synthetic opportunities offered by anti .alpha.-methylene-.beta.-hydroxy-.gamma.-alkoxy esters: stereoselective reactions at the double bond
  作者：Anna Bernardi、Maria Grazia Beretta、Lino Colombo、Cesare Gennari、Giovanni Poli、Carlo Scolastico

  DOI：10.1021/jo00223a005

  日期：1985.11
• Stereoselective titanium-mediated aldol reactions of (S)-2-tert-butyldimethylsilyloxy-3-pentanone
  作者：Joaquim Nebot、Sergi Figueras、Pedro Romea、Fèlix Urpí、Yining Ji

  DOI：10.1016/j.tet.2006.09.034

  日期：2006.11

  Titanium-mediated aldol reactions based on (S)-2-tert-butyldimethylsilyloxy-3-pentanone, a lactate-derived chiral ketone, provide the corresponding 2,4-syn-4,5-syn adducts in high yields and diastereomeric ratios with a wide array of achiral and chiral aldehydes. Furthermore, spectroscopic studies of intermediates involved in the process have permitted to propose a mechanism that accounts for the experimental results. (c) 2006 Elsevier Ltd. All rights reserved.
• BERNARDI, A.;BERETTA, M. G.;COLOMBO, L.;GENNARI, C.;POLI, G.;SCOLASTICO, +, J. ORG. CHEM., 1985, 50, N 23, 4442-4447
  作者：BERNARDI, A.、BERETTA, M. G.、COLOMBO, L.、GENNARI, C.、POLI, G.、SCOLASTICO, +

  DOI：——

  日期：——
• GENNARI, C.;BERNARDI, A.;CARDANI, S.;SCOLASTICO, C., TETRAHEDRON, 1984, 40, N 20, 4059-4065
  作者：GENNARI, C.、BERNARDI, A.、CARDANI, S.、SCOLASTICO, C.

  DOI：——

  日期：——