(2R,3R,4S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one | 1307782-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2R,3R,4S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: (2R,3R,4S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)-3,4-dihydronaphthalen-1-one
• CAS: 1307782-04-2
• 化学式: C₂₈H₃₂O₅Si
• 分子量: 476.645
• InChiKey: PVWISESMCBQBTR-MPYJOUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one 在 sodium tetrahydroborate 、 水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 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
• 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 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 (2R,3R,4S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one
  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

文献信息

• Asymmetric synthesis of aryl cyclitols based on 1,2,3,4-tetrahydronaphthalene scaffolds
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2011.02.009

  日期：2011.2

  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.