(1S,2R,3S,4S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-1,2,3,4-tetrahydronaphthalene-1,2,4-triol | 1307781-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1S,2R,3S,4S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-1,2,3,4-tetrahydronaphthalene-1,2,4-triol
• 英文别名: (1S,2R,3S,4S)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(hydroxymethyl)-2,4-dihydro-1H-naphthalene-1,2,4-triol
• CAS: 1307781-54-9
• 化学式: C₂₈H₃₄O₅Si
• 分子量: 478.66
• InChiKey: STFYATAQXJQHGR-OBXRUURASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  acetic acid (S)-4-bromo-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmethyl ester 在 sodium tetrahydroborate 、 四氧化锇 、 potassium carbonate 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 51.0h， 生成 (1S,2R,3S,4S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-1,2,3,4-tetrahydronaphthalene-1,2,4-triol
  参考文献：
  名称：

  Asymmetric synthesis of aryl cyclitols based on 1,2,3,4-tetrahydronaphthalene scaffolds

  摘要：

  A series of aryl cyclitols based on a 1,2,3,4-tetrahydronaphthalene scaffold have been synthesized in a stereocontrolled manner. These cyclitols possess four contiguous stereocenters amongst which one is a quaternary stereocenter, which has been constructed by applying enzymatic kinetic resolution reaction. The remaining stereocenters have been created by substrate directed asymmetric dihydroxylation reaction and stereoselective keto-reduction process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.009