(R)-(-)-(tosyloxy)-3,3-dimethyl-butan-2-ol | 40348-71-8

• 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)-(-)-(tosyloxy)-3,3-dimethyl-butan-2-ol
• 英文别名: [(2R)-2-hydroxy-3,3-dimethylbutyl] 4-methylbenzenesulfonate
• CAS: 40348-71-8
• 化学式: C₁₃H₂₀O₄S
• 分子量: 272.365
• InChiKey: LFBGJKFVTSISIE-LBPRGKRZSA-N

物化性质

• 沸点：
  402.4±28.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-(tosyloxy)-3,3-dimethyl-butan-2-ol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以41%的产率得到(R)-tert-butyloxirane
  参考文献：
  名称：

  Early Transition Metal Alkoxide Complexes Bearing Homochiral Trialkanolamine Ligands

  摘要：

  Enantiomerically pure trialkanolamines of the formula N(CH(2)CHROH)(3), where R = methyl (3a), cyclohexyl (3b), tert-butyl (3c), or phenyl (3d), are readily synthesized by the reaction of ammonia with 3 equiv of an enantiopure epoxide. Trialkanolamines 3a-d replace n-propanol in tri-n-propyl vanadate to afford corresponding complexes 4a-d of the formula LV=O, where L is the deprotonated trialkanolamine. Similarly, (S,S,S)-triisopropanolamine 3a reacts with Ti((OPr)-Pr-i)(4) to produce monomeric LTi((OPr)-Pr-i), 7a, which upon treatment with acetyl chloride gives the chloro complex LTiCl, 7b. The later group 5 ethoxides react with 3a to produce LM(OEt)(2) (M = Nb, Ta). Partial hydrolysis of the Nb and Ta derivatives produces tetrameric mu-oxo-bridged structures which retain the trialkanolamine ligands. In all complexes the transition metal resides in a highly asymmetric environment, suggesting that this class of complexes may find use in the field of asymmetric catalysis. The X-ray crystal structures of complexes 4c and 7b are reported.

  DOI：

  10.1021/ja00093a011
• 作为产物：
  描述：

  (R)-3,3-dimethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]butan-1-ol p-tosylate 在 Amberlite IR-120 (H⁺ form) 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到(R)-(-)-(tosyloxy)-3,3-dimethyl-butan-2-ol
  参考文献：
  名称：

  Enantiomerically pure chiral pyridino-crown ethers: synthesis and enantioselectivity toward the enantiomers of α-(1-naphthyl)ethylammonium perchlorate

  摘要：

  Seven new enantiomerically pure chiral pyridino-crown ethers (S,S)-4-(R,R)-10 were prepared. Three of them [(S,S)-4, (S,S)-7 and (R,R)-10] contain one, and two of them [(S,S)-5 and (S,S)-8] contain two linker chains with a terminal double bond. These linker chains were connected to the carbon atom at position 9 (opposite the pyridine moiety) of the macrocycle. The terminal double bond of the linker makes it possible to attach these ligands to silica gel to obtain chiral stationary phases (CSPs). The enantioselectivity of the new ligands toward the enantiomers of alpha-(1-naphthyl)ethylammonium perchlorate (NEA) was also determined by a titration H-1 NMR method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00381-x

文献信息

• [EN] ALPHA-KETOAMIDE DERIVATIVES AS CATHEPSIN K INHIBITORS<br/>[FR] DERIVES D'ALPHA-CETOAMIDE UTILISES EN TANT QU'INHIBITEURS DE LA CATHEPSINE K
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2003013518A1

  公开（公告）日：2003-02-20

  Biaryl ketoamide derivatives (I), which are useful as cathepsin K inhibitors are described herein. The described invention also includes methods of making such biaryl ketoamide derivatives as well as methods of using the same in the treatment of disorders, including osteoporosis, associated with enhanced bone turnover which can ultimately lead to fracture.

  本文描述了有用于作为蛋白酶K抑制剂的双芳基酮酰胺衍生物(I)。所述的发明还包括制备这种双芳基酮酰胺衍生物的方法，以及在治疗与增强骨转换相关的疾病，包括骨质疏松症，最终可能导致骨折的方法。
• Alpha-ketoamide derivatives as cathepsin k inhibitors
  申请人：Barrett David Gene

  公开号：US20050107616A1

  公开（公告）日：2005-05-19

  Biaryl ketoamide derivatives, which are useful as cathepsin K inhibitors are described herein. The described invention also includes methods of making such biaryl ketoamide derivatives as well as methods of using the same in the treatment of disorders, including osteoporosis, associated with enhanced bone turnover which can ultimately lead to fracture.

  本文介绍了用作猫hepsin K抑制剂的联苯基酮酰胺衍生物。所述发明还包括制备这种联苯基酮酰胺衍生物的方法，以及将其用于治疗与增强骨转换有关的疾病，包括骨质疏松症，该疾病最终可能导致骨折的方法。
• Propylcarbamate derivatives as inhibitors of serine and cysteine proteases
  申请人：Deaton Norman David

  公开号：US20050043368A1

  公开（公告）日：2005-02-24

  The present invention includes ketone derivatives (I) and (II), which are useful as cathepsin K inhibitors. The described invention also includes methods of making such ketone derivatives as well as methods of using the same in the treatment of disorders, including osteoporosis.

  本发明涉及酮衍生物（I）和（II），其作为猫hepsin K抑制剂具有用途。所述发明还包括制备此类酮衍生物的方法，以及使用它们治疗疾病的方法，包括骨质疏松症。
• (2S,2′R)-Analogue of LG190178 is a major active isomer
  作者：Wataru Hakamata、Yukiko Sato、Haruhiro Okuda、Shinobu Honzawa、Nozomi Saito、Seishi Kishimoto、Atsushi Yamashita、Takayuki Sugiura、Atsushi Kittaka、Masaaki Kurihara

  DOI：10.1016/j.bmcl.2007.11.007

  日期：2008.1

  Vitamin D receptor (VDR) ligands are therapeutic agents for the treatment of psoriasis, osteoporosis, and secondary hyperparathyroidism. VDR ligands also show immense potential as therapeutic agents for autoimmune diseases and cancers of the skin, prostate, colon, and breast as well as leukemia. LG190178 is a novel non-secosteroidal ligand for VDR. We synthesized and evaluated stereoisomers of LG190178 and found that only an (2S,2'R)-analogue of LG190178 (YR301) had strong activity. (C) 2007 Elsevier Ltd. All rights reserved.
• ALPHA-KETOAMIDE DERIVATIVES AS CATHEPSIN K INHIBITORS
  申请人：SmithKline Beecham Corporation

  公开号：EP1411933A1

  公开（公告）日：2004-04-28