(6S,7R,8S,8aR)-6,7,8-trihydroxy-hexahydrooxazolo[3,4-a]pyridin-3(5H)-one | 1221569-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (6S,7R,8S,8aR)-6,7,8-trihydroxy-hexahydrooxazolo[3,4-a]pyridin-3(5H)-one
• 英文别名: (6S,7R,8S,8aR)-6,7,8-trihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one；(6S,7R,8S,8aR)-6,7,8-trihydroxy-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 1221569-14-7
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: GTTBBVFZKUCUGG-DPYQTVNSSA-N

物化性质

• 沸点：
  471.6±45.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6S,7R,8S,8aR)-6,7,8-trihydroxy-hexahydrooxazolo[3,4-a]pyridin-3(5H)-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 米加司他
  参考文献：
  名称：

  I 2介导的氨基甲酸酯环在哌啶合成中的应用和局限性：五元环与六元环的形成

  摘要：

  已经探索了用于合成哌啶的无保护基的合成策略。在合成关键是I 2介导的氨基甲酸酯环，其允许羟基取代alkenylamines的环化成哌啶，吡咯烷，和呋喃。在这项工作中，4个手性支架，比较和对比，并且据观察，与两个d半乳糖和2-脱氧d半乳糖作为原料，将变换到是哌啶-1- deoxygalactonorjirimycin（DGJ）和4-外延-可以通过几个步骤和良好的总收率分别获得fagomine。当d葡萄糖被用作起始材料，只有呋喃产物形成，而使用2-脱氧的d-葡萄糖导致化学和立体选择性的降低以及四种产物的形成。可以提供每种环糊精产物形成的机理解释，这有助于我们更好地理解哌啶合成中氨基甲酸酯环糊精的范围和局限性。

  DOI：

  10.1021/jo401512h
• 作为产物：
  描述：

  methyl 6-deoxy-6-iodo-α-D-galactopyranoside 在 ammonium acetate 、 氨 、 碘 、 sodium cyanoborohydride 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 114.0h， 生成 (6S,7R,8S,8aR)-6,7,8-trihydroxy-hexahydrooxazolo[3,4-a]pyridin-3(5H)-one 、 (6S,7R,8S,8aS)-6,7,8-trihydroxy-hexahydrooxazolo[3,4-a]pyridin-3(5H)-one 、 (1R,7S,8S,9R)-8,9-dihydroxy-3,10-dioxa-5-azabicyclo[5.2.1]decan-4-one
  参考文献：
  名称：

  Rapid synthesis of 1-deoxygalactonojirimycin using a carbamate annulation

  摘要：

  A remarkably efficient synthesis of the biologically important iminosugar 1-deoxygalactonojirimycin (DGJ) is presented. Key to this strategy is the development of a novel carbamate annulation reaction that favours formation of a six-membered carbamate-containing piperidine skeleton over its five-membered counterpart. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.044

文献信息

• [EN] METHODS FOR THE PREPARATION OF ALKENYLAMINES, CYCLIC CARBAMATES OR DITHIOCARBAMATES, AND AMINOALCOHOLS OR AMINOTHIOLS<br/>[FR] PROCÉDÉS POUR LA PRÉPARATION D'ALCÉNYLAMINES, DE CARBAMATES CYCLIQUES OU DE DITHIOCARBAMATES, ET D'AMINOALCOOLS OU D'AMINOTHIOLS
  申请人：VICTORIA LINK LTD

  公开号：WO2010041964A1

  公开（公告）日：2010-04-15

  A method for preparing an alkenylamine, or a salt, solvate or hydrate thereof, is disclosed. The method comprises reacting a alogen-substituted cyclic acetal or a derivative thereof under particular conditions to provide the alkenylamine, which may be optionally converted into a salt, solvate or hydrate thereof. A method for preparing a cyclic carbamate or cyclic dithiocarbamate, or a salt, solvate or hydrate thereof, is also disclosed. The method comprises reacting an alkenylamine under particular conditions to provide the cyclic carbamate or cyclic dithiocarbamate, which may be optionally converted into a salt, solvate or hydrate thereof. A method for preparing a 1,2-aminoalcohol or 1,2-aminothiol, or a salt, solvate or hydrate thereof, is also disclosed. The method comprises forming a cyclic carbamate or cyclic dithiocarbamate from an alkenylamine, and deprotecting the cyclic carbamate or cyclic dithiocarbamate to provide the 1,2-aminoalcohol or 1,2-aminothiol, which may optionally be converted into a salt, solvate or hydrate thereof.

  揭示了一种制备烯基胺或其盐、溶剂合物或水合物的方法。该方法包括在特定条件下反应氯代取代的环缩醛或其衍生物以提供烯基胺，该烯基胺可以选择性地转化为其盐、溶剂合物或水合物。还揭示了一种制备环氨基甲酸酯或环二硫代氨基甲酸酯或其盐、溶剂合物或水合物的方法。该方法包括在特定条件下反应烯基胺以提供环氨基甲酸酯或环二硫代氨基甲酸酯，该化合物可以选择性地转化为其盐、溶剂合物或水合物。还揭示了一种制备1,2-氨基醇或1,2-氨基硫醇或其盐、溶剂合物或水合物的方法。该方法包括从烯基胺中形成环氨基甲酸酯或环二硫代氨基甲酸酯，并去保护环氨基甲酸酯或环二硫代氨基甲酸酯以提供1,2-氨基醇或1,2-氨基硫醇，该化合物可以选择性地转化为其盐、溶剂合物或水合物。
• SUGAR DERIVATIVES COMPRISING SULFUR-CONTAINING MOIETIES AND METHODS OF MAKING SAME AND METHODS OF USING THE SAME FOR THE TREATMENT OF MPS IIIC
  申请人：Amicus Therapeutics, Inc.

  公开号：EP3105235B1

  公开（公告）日：2019-11-06
• Sugar Derivatives Comprising Sulfur-Containing Moieties And Methods Of Making Same and Methods of Using the Same for the Treatment of MPS IIIC
  申请人：Amicus Therapeutics, Inc.

  公开号：US20150225420A1

  公开（公告）日：2015-08-13

  Described herein are modified sugar, iminosugar and azasugar compounds and methods of making same. One or more of these modified compounds contain sulfates, sulfites, sulfamates and/or sulfonamides. Also described are pharmaceutical compositions/formulations comprising these compounds, as well as methods using these modified sugar compounds for the treatment of MPS IIIC (also known as Sanfilippo Type C).
• Sugar Derivatives Comprising Sulfur-Containing Moieties And Methods Of Making Same And Methods Of Using The Same For The Treatment Of MPS IIIC
  申请人：Amicus Therapeutics, Inc.

  公开号：US20170190665A1

  公开（公告）日：2017-07-06

  Described herein are modified sugar, iminosugar and azasugar compounds and methods of making same. One or more of these modified compounds contain sulfates, sulfites, sulfamates and/or sulfonamides. Also described are pharmaceutical compositions/formulations comprising these compounds, as well as methods using these modified sugar compounds for the treatment of MPS IIIC (also known as Sanfilippo Type C).
• US9598438B2
  申请人：——

  公开号：US9598438B2

  公开（公告）日：2017-03-21