(R)-3-<(tetrahydro-2H-pyranyl)oxy>butyl p-toluenesulfonate | 77564-43-3

• 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: (R)-3-<(tetrahydro-2H-pyranyl)oxy>butyl p-toluenesulfonate
• 英文别名: (R)-3-tetrahydropyranyloxy-1-butyl tosylate；(R)-3-(tetrahydropyranyloxy)butyl tosylate；(R)-3-tetrahydropyranosyloxybutyl tosylate；(R)-1,3-butanediol 1-tosylate 3-THP ether；(R)-3-tetrahydropyranyloxybutyl tosylate；[(3R)-3-(oxan-2-yloxy)butyl] 4-methylbenzenesulfonate
• CAS: 77564-43-3
• 化学式: C₁₆H₂₄O₅S
• 分子量: 328.43
• InChiKey: SRUPJAVHSMMLFB-IURRXHLWSA-N

物化性质

• 沸点：
  471.4±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-3-<(tetrahydro-2H-pyranyl)oxy>butyl p-toluenesulfonate 在 sodium hydroxide 作用下， 以 乙醚 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl (R)-4-tetrahydropyranyloxypentanoate
  参考文献：
  名称：

  Kitahara, Takeshi; Koseki, Koshi; Mori, Kenji, Agricultural and Biological Chemistry, 1983, vol. 47, # 2, p. 389 - 394

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-3-tetrahydropyranyloxy-1-butanol 以81.9%的产率得到(R)-3-<(tetrahydro-2H-pyranyl)oxy>butyl p-toluenesulfonate
  参考文献：
  名称：

  合成3,2,8-二甲基-1,7-dioxaspiro [5.5]十一烷的立体异构形式，Andrena wilkella头分泌的主要成分

  摘要：

  利用乙酰乙酸酯的酵母还原和二价阴离子烷基化反应，从乙酰乙酸酯合成了2,8-二甲基-1,7-二氧杂螺[5,5]十一烷的三种立体异构体。

  DOI：

  10.1016/s0040-4020(01)98857-x

文献信息

• Synthesis of the propionates of (2r, 8r)- and (2s, 8r)-8-methyl-2-decanol, the pheromone of the western corn rootworm, employing chiral compounds of microbial origin as starting materials
  作者：Kenji Mori、Hindenori Watanabe

  DOI：10.1016/s0040-4020(01)91175-5

  日期：1984.1

  The attractants of the western corn rootworm (Diabrotica virgiferaLe Counte), the propionates of (2R, 8R)-and (2S, 8R)-8-methyl-2-decanol, were synthesized from (R)-(+)-citronellol and the enantiomers of ethyl β-hydroxybutryate of microbial origin.

  由（R）-（+）-香茅醇合成西部玉米根虫（Diabrotica virgifera Le Counte）的引诱剂，（2R，8R）-和（2S，8R）-8-甲基-2-癸醇的丙酸酯。和微生物来源的β-羟基丁酸乙酯的对映体。
• Mori, Kenji; Tanida, Kaichi, Heterocycles, 1981, vol. 15, # 2, p. 1171 - 1174
  作者：Mori, Kenji、Tanida, Kaichi

  DOI：——

  日期：——
• Mori, Kenji; Soga, Hiroshi; Ikunaka, Masaya, Liebigs Annalen der Chemie, 1985, # 11, p. 2194 - 2205
  作者：Mori, Kenji、Soga, Hiroshi、Ikunaka, Masaya

  DOI：——

  日期：——
• Pinyarat, Waraporn; Mori, Kenji, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 10, p. 1673
  作者：Pinyarat, Waraporn、Mori, Kenji

  DOI：——

  日期：——
• Enantioselective Fluorogenic Assay of Acetate Hydrolysis for Detecting Lipase Catalytic Antibodies
  作者：Gérard Klein、Jean-Louis Reymond

  DOI：10.1002/(sici)1522-2675(19990310)82:3<400::aid-hlca400>3.0.co;2-c

  日期：1999.3.10

  An enantioselective fluorogenic assay for the kinetic resolution of chiral alkyl acetates is demonstrated with 7-(3-aceroxybutoxy)-2H-1-henzopyran-2-ones (R)- and (S)-4 or 7-(3-acetoxy-2-methylpropoxy)-2H-1-benzopyran-2-ones (R)-4 and (S)-6. The alcohols released by hydrolysis of these acetates are oxidized by horse-liver alcohol dehydrogenase to unstable beta-(aryloxy)carbonyl compounds: which undergo beta-elimination of the strongly fluorescent product umbelliferone (= 7-hydroxy-2H-1-benzopyran-2-one; 3) (lambda(em) = 460 +/- 20 nm, lambda(ex) = 360 +/- 20 nm). Enantioselectivities are calculated from the reaction rates for each enantiomeric acetate. For a series of representative lipases, the reactivities and enantioselectivities under preparative conditions are predicted accurately. This highly sensitive enantioselective assay detects as little as 10 mu g/ml of hydrolytic enzyme, can be carried out in 96-well microtiter plates. and is compatible with cell-cult Ire media. It is, therefore, suited for screening libraries of antibodies for enantioselective lipase catalytic antibodies.