(2R)-2-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[tert-butyl(dimethyl)silyl]oxybut-3-en-2-ol | 148236-80-0

• 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: (2R)-2-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[tert-butyl(dimethyl)silyl]oxybut-3-en-2-ol
• CAS: 148236-80-0
• 化学式: C₂₄H₃₈O₆Si
• 分子量: 450.648
• InChiKey: QKZYAKQRJJMPMZ-XQWURTRYSA-N

物化性质

• 沸点：
  495.1±45.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[tert-butyl(dimethyl)silyl]oxybut-3-en-2-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2R)-2-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]but-3-ene-1,2-diol
  参考文献：
  名称：

  A formal synthesis of a novel immunosuppressant ISP-1 : Stereocontrolled Pd(O) catalysed -hydroxyamination of carbohydrate derived vinyl epoxide

  摘要：

  Described herein are the results leading to the synthesis of ISP-1 containing an unusal alpha, alpha-disubstituted amino acid and whose immunosuppressive activity only has recently been discovered.

  DOI：

  10.1016/0040-4039(93)85033-s
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2R)-2-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[tert-butyl(dimethyl)silyl]oxybut-3-en-2-ol
  参考文献：
  名称：

  A formal synthesis of a novel immunosuppressant ISP-1 : Stereocontrolled Pd(O) catalysed -hydroxyamination of carbohydrate derived vinyl epoxide

  摘要：

  Described herein are the results leading to the synthesis of ISP-1 containing an unusal alpha, alpha-disubstituted amino acid and whose immunosuppressive activity only has recently been discovered.

  DOI：

  10.1016/0040-4039(93)85033-s

文献信息

• A New Stereoselective Route to Chiral Tertiary Alcohols in Water
  作者：Teck-Peng Loh、Diana Ho、Guan-Leong Chua、Keng-Yeow Sim

  DOI：10.1055/s-1997-3230

  日期：1997.5

  A new and simple preparation of chiral tertiary alcohols via the indium-mediated allylation of sugar-derived ketones in water is described.

  本文描述了一种在水相中通过铟介导的糖源性酮的烯丙基化反应，制备手性叔醇的新颖且简便的方法。
• Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue
  作者：Yves Blériot、Subramanian K. Vadivel、Antonio J. Herrera、Ian R. Greig、Anthony J. Kirby、Pierre Sinaÿ

  DOI：10.1016/j.tet.2004.06.009

  日期：2004.8

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of B2,5 type conformationally constrained glucopyranosides
  作者：Yves Blériot、Subramanian K Vadivel、Ian R Greig、Anthony J Kirby、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(03)01631-9

  日期：2003.8

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides restrained in a conformation close to B-2,B-5 have been synthesized. They are all hydrolyzed at similar rates, close to those observed for the parent unlocked glucosides. (C) 2003 Elsevier Ltd. All rights reserved.