(3R,5S,1'R)-3-(t-butyldimethylsilyloxy)-5-hydroxy-5-(1'-phenylethoxy) pentanoic acid lactone | 459870-98-5

• 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: (3R,5S,1'R)-3-(t-butyldimethylsilyloxy)-5-hydroxy-5-(1'-phenylethoxy) pentanoic acid lactone
• 英文别名: (4R,6S)-4-((tert-butyldimethylsilyl)oxy)-6-((R)-1-phenylethoxy)tetrahydro-2H-pyran-2-one；(4R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(1R)-1-phenylethoxy]oxan-2-one
• CAS: 459870-98-5
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: HFFIVTZEEUMNGX-HFTRVMKXSA-N

物化性质

• 沸点：
  421.9±45.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S,1'R)-3-(t-butyldimethylsilyloxy)-5-hydroxy-5-(1'-phenylethoxy) pentanoic acid lactone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate
  参考文献：
  名称：

  Desymmetrisation of dialdehydes: (+)-(S) and (−)-(R) nor-methyl mevaldate as versatile synthetic intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(02)00533-6
• 作为产物：
  描述：

  1,6-庚二烯-4-醇 在 咪唑 、 臭氧 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 106.42h， 生成 (3R,5S,1'R)-3-(t-butyldimethylsilyloxy)-5-hydroxy-5-(1'-phenylethoxy) pentanoic acid lactone
  参考文献：
  名称：

  nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one

  摘要：

  Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96: 4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.048

文献信息

• Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (−) nor-mevalonic lactones
  作者：José Manuel Botubol-Ares、María Jesús Durán-Peña、Rosario Hernández-Galán、Isidro G. Collado、Laurence M. Harwood、Antonio J. Macías-Sánchez

  DOI：10.1016/j.tet.2015.08.010

  日期：2015.10

  Solvent-free desymmetrisation of a meso-dialdehyde with chiral alcohols, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one derivatives with a 96% de. This methodology, which yields the corresponding methyl nor-mevaldates with 99% ee, has been applied to the enantioselective synthesis of the (−)-(R) and (+)-(S) nor-mevalonic acid lactones.

  的无溶剂的去对称内消旋-dialdehyde与手性醇，导致制备的4-甲硅烷氧基-6- alkyloxytetrahydro -2- ħ -吡喃-2-酮用96％去衍生物。该方法可产生具有99％ee的相应甲基正甲羟戊酸酯，已应用于（-）-（R）和（+）-（S）甲羟戊酸内酯的对映选择性合成。