phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone | 158812-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone
• 英文别名: [(2R)-3-(benzenesulfonyl)-2-methylpropoxy]-tert-butyl-diphenylsilane
• CAS: 158812-78-3
• 化学式: C₂₆H₃₂O₃SSi
• 分子量: 452.69
• InChiKey: AVTFNWJNRSUTBJ-JOCHJYFZSA-N

物化性质

• 沸点：
  548.7±46.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以91%的产率得到(2R)-2-methyl-3-(phenylsulfonyl)propan-1-ol
  参考文献：
  名称：

  Total Synthesis of Polycavernoside A, A Lethal Toxin of the Red Alga Polycavernosa tsudai

  摘要：

  Two approaches to the synthesis of the aglycon 120 of polycavernoside A (1) were developed, only one of which was completed. The successful "second-generation" route assembled the aglycon seco acids 102 and 106 via Nozaki-Hiyama-Kishi coupling of aldehyde 70, prepared from methyl (S)3-hydroxy-2-methylpropionate (72) and (S)-pantolactone (73), with vinyl bromide 71. The latter was obtained from a sequence which commenced from the silyl ether 24 of 3-hydroxypropionaldehyde and entailed cyclization of (Z)-zeta -hydroxy-alpha,beta-unsaturated ester 82. Regioselective Yamaguchi lactonization of trihydroxycarboxylic acids 102 and 106 and subsequent functional-group adjustments led to macrolactone 120, to which the fucopyranosylxylopyranoside moiety was attached. Stille coupling of the glycosidated aglycon 128 with dienylstannane 129 furnished polycavernoside A in a synthesis for which the longest linear sequence was 25 steps. The overall yield to lactone 120 was 4.7%.

  DOI：

  10.1021/jo0503862
• 作为产物：
  描述：

  (R)-3-[(tert-butyl)diphenylsilyloxy]-1-iodo-2-methylpropane 在 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone
  参考文献：
  名称：

  芸苔素内酯的正式合成

  摘要：

  酶催化的C 2v形四醇-硫化物中羟基的分化，结合E-立体收敛的Ramberg-Bäcklund工艺，可以制备纯净的（2 S）-2,3-二甲基-1-碘丁烷加上3,5-环戊烯-20-硫代甲醇衍生物，以提供标题植物激素的有效前体。

  DOI：

  10.1016/s0040-4039(97)00474-7

文献信息

• Synthetic routes to campesterol and dihydrobrassicasterol: a first reported synthesis of the key phytosterol dihydrobrassicasterol
  作者：N.M. O'Connell、Y.C. O'Callaghan、N.M. O'Brien、A.R. Maguire、F.O. McCarthy

  DOI：10.1016/j.tet.2012.04.060

  日期：2012.6

  Phytosterols are increasingly used as health supplements in functional foods and are associated with having both positive and negative effects on health. Given this disparity, an investigation of their full individual biological profile is imperative in order to assure food safety. This paper describes the de novo synthesis of pure phytosterols in multigram scale and we report the first synthesis of

  植物甾醇越来越多地用作功能性食品中的健康补充剂，并且与对健康的正面和负面影响有关。考虑到这种差异，必须对其完整的个体生物学特性进行调查，以确保食品安全。本文以毫克级从头开始描述纯植物甾醇的从头合成，并且我们报告了关键植物甾醇二氢Brassicasterol的首次合成以及与菜油甾醇的路线比较。包括对化合物，混合物及其前体的13 C NMR光谱数据的完整分配，进行了详细的光谱分析，从而潜在地将NMR光谱用作分析这些固醇混合物的工具。
• Reductive lithiation of bis-phenylsulfones
  作者：Jurong Yu、Hyun-Sung Cho、S. Chandrasekhar、J.R. Falck、Charles Mioskowski

  DOI：10.1016/s0040-4039(00)73519-2

  日期：1994.7

  Reductive cleavage of geminal bis-phenylsulfones using lithium naphthalenide in THF at -78 degrees C selectively affords alpha-sulfonyl carbanions which participate in typical reaction with electrophiles.
• Toward a total synthesis of an aglycone of spiramycin; installation of the hydroxy groups at C-4 and C-5: a model study
  作者：G Oddon、D Uguen、A De Cian、J Fischer

  DOI：10.1016/s0040-4039(97)10760-2

  日期：1998.3

  The stereochemical course of the osmium-mediated bis-hydroxylation of the allylic derivative 6c, whose the structure is closely related to that of a C-1/C-7 fragment of the title aglycone, has been established unambiguously by X-ray analysis of a carboxylic acid derived from one of the two diastereomeric dials which formed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Yu Jurong, Cho Hyun-Sung, Chandrasekhar S., Falck J. R., Mioskowski Charl+, Tetrahedron Lett, 35 (1994) N 30, S 5437-5440
  作者：Yu Jurong, Cho Hyun-Sung, Chandrasekhar S., Falck J. R., Mioskowski Charl+

  DOI：——

  日期：——
• Total Synthesis of Polycavernoside A, A Lethal Toxin of the Red Alga <i>Polycavernosa </i><i>t</i><i>sudai</i>
  作者：Paul R. Blakemore、Cindy C. Browder、Jian Hong、Christopher M. Lincoln、Pavel A. Nagornyy、Lonnie A. Robarge、Duncan J. Wardrop、James D. White

  DOI：10.1021/jo0503862

  日期：2005.7.1

  Two approaches to the synthesis of the aglycon 120 of polycavernoside A (1) were developed, only one of which was completed. The successful "second-generation" route assembled the aglycon seco acids 102 and 106 via Nozaki-Hiyama-Kishi coupling of aldehyde 70, prepared from methyl (S)3-hydroxy-2-methylpropionate (72) and (S)-pantolactone (73), with vinyl bromide 71. The latter was obtained from a sequence which commenced from the silyl ether 24 of 3-hydroxypropionaldehyde and entailed cyclization of (Z)-zeta -hydroxy-alpha,beta-unsaturated ester 82. Regioselective Yamaguchi lactonization of trihydroxycarboxylic acids 102 and 106 and subsequent functional-group adjustments led to macrolactone 120, to which the fucopyranosylxylopyranoside moiety was attached. Stille coupling of the glycosidated aglycon 128 with dienylstannane 129 furnished polycavernoside A in a synthesis for which the longest linear sequence was 25 steps. The overall yield to lactone 120 was 4.7%.