2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone | 69992-14-9

• 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: 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone
• 英文别名: (2S,3R,5R)-2-methyl-6-oxotetrahydro-2H-pyran-3,5-diyl dibenzoate；[(2S,3R,5R)-5-benzoyloxy-2-methyl-6-oxooxan-3-yl] benzoate
• CAS: 69992-14-9
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: GWAJSJIUDSHXOO-IAOVAPTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone 生成 (2S,3R,5R)-5-(benzoyloxy)-6-hydroxy-2-methyloxan-3-yl benzoate
  参考文献：
  名称：

  消除内齿内酯中的β。3,6-二脱氧L-阿拉伯糖基己糖（a糖）的合成

  摘要：

  摘要用过量的苯甲酰氯和吡啶将L-鼠李糖1,5-内酯（1）苯甲酰化16小时，得到2,4-O-苯甲酰基-3,6-二脱氧-L-赤-己二-2-enono -1，5-内酯（2）。2的催化氢化是立体选择性的，得到结晶的2,4-二-O-苯甲酰基-3,6-二脱氧-L-阿拉伯糖-己基-1,5-内酯（3）。用二亚氨基硼烷还原内酯3可获得2,4-二-O-苯甲酰基-3,6-二脱氧-L-阿拉伯-己吡喃糖（4），在脱苯甲酰化后，得到3,6-二脱氧-L-阿拉伯-己糖（总收率良好）。该糖经鉴定为相应的醛糖醇（scar糖醇），并通过转化为甲基3,6-二脱氧-α-L-阿糖基-己吡喃糖苷（甲基Ascaryloside，6）。

  DOI：

  10.1016/s0008-6215(00)83267-x
• 作为产物：
  描述：

  2,4-di-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以96%的产率得到2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone
  参考文献：
  名称：

  Improved Synthesis of an Ascaroside Pheromone Controlling Dauer Larva Development in Caenorhabditis elegans

  摘要：

  利用高效的瓦克氧化法作为关键步骤，我们描述了一种经过显著改进的促进矮小的阿斯卡甙 2 的合成方法，用于新型甾醇环甲基化酶 STRM-1 的生物学研究。

  DOI：

  10.1055/s-0029-1216967

文献信息

• [EN] 6R-(3,6-DIDEOXY-L-ARABINO-HEXOPYRANOSYLOXY)HEPTANOIC ACID, PREPARATION PROCESS FOR THE SAME AND DAUER EFFECT THEREOF<br/>[FR] ACIDE 6R-(3,6-DIDESOXY-L-ARABINO-HEXOPYRANOSYLOXY)HEPTANOIQUE, PROCEDE DE PREPARATION DE CET ACIDE ET EFFET DAUER DE CET ACIDE
  申请人：JUNG MANKIL

  公开号：WO2005075491A1

  公开（公告）日：2005-08-18

  The present invention relates to a determination of a stereochemistry, a synthesis and dauer effect of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy) heptanoic acid as a pheromone isolated from the Caenorhabditis elegance related to suppress of aging and stress. It becomes possible to develop medical substances using the pheromone relating to aging, stress, metabolism, signal transfer system in vivo, and anti-cancer, obesity and a suppressing agent for aging and stress.

  本发明涉及一种从Caenorhabditis elegans中分离出的6R-(3,6-二去氧-L-阿拉伯糖基)庚酸酯素的立体化学确定、合成和抑制老化和应激的效果。利用与老化、应激、新陈代谢、体内信号传递系统以及抗癌、肥胖和抑制老化和应激的药剂相关的这种信息素，可以研发出医药物质。
• 6R-(3,6-dideoxy-l-Arabino-Hexopyranosyloxy) heptanoic acid, preparation process for the same and dauer effect thereof
  申请人：Jung Mankil

  公开号：US20060079465A1

  公开（公告）日：2006-04-13

  The present invention relates to a determination of a stereochemistry, a synthesis and dauer effect of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy)heptanoic acid as a pheromone isolated from the Caenorhabditis elegance related to suppress of aging and stress. It becomes possible to develop medical substances using the pheromone relating to aging, stress, metabolism, signal transfer system in vivo, and anti-cancer, obesity and a suppressing agent for aging and stress.

  本发明涉及从秀丽隐杆线虫中分离出的一种信息素6R-(3,6-二脱氧-L-阿拉伯糖基)庚酸的立体化学确定、合成和持久效应，该信息素与抑制衰老和压力有关。使用与衰老、压力、体内代谢、信号传递系统以及抗癌、肥胖和抑制衰老和压力的药物有关的信息素，可以开发医学物质。
• 6R-(3,6-DIDEOXY-L-ARABINO-HEXOPYRANOSYLOXY) HEPTANOIC ACID, PREPARATION PROCESS FOR THE SAME AND DAUER EFFECT THEREOF
  申请人：Jung Mankil

  公开号：US20080188646A1

  公开（公告）日：2008-08-07

  The present invention relates to a determination of a stereochemistry, a synthesis and dauer effect of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy)heptanoic acid as a pheromone isolated from the Caenorhabditis elegance related to suppress of aging and stress. It becomes possible to develop medical substances using the pheromone relating to aging, stress, metabolism, signal transfer system in vivo, and anti-cancer, obesity and a suppressing agent for aging and stress.

  本发明涉及从秀丽隐杆线虫中分离出的一种信息素6R-(3,6-二脱氧-L-阿拉伯糖基)庚酸的立体化学确定、合成和抑制衰老和压力相关性的达尔效应。利用与衰老、压力、体内代谢、信号传递系统、抗癌、肥胖以及抑制衰老和压力的药物相关的信息素，开发医药物质成为可能。
• 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy) heptanoic acid, preparation process for the same and dauer effect thereof
  申请人：KDR Biotech. Co. Ltd.

  公开号：US07576225B2

  公开（公告）日：2009-08-18

  The present invention relates to a determination of a stereochemistry, a synthesis and dauer effect of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy) heptanoic acid as a pheromone isolated from the Caenorhabditis elegance related to suppress of aging and stress. It becomes possible to develop medical substances using the pheromone relating to aging, stress, metabolism, signal transfer system in vivo, and anti-cancer, obesity and a suppressing agent for aging and stress.

  本发明涉及一种立体化学的确定，6R-(3,6-二脱氧-L-阿拉伯糖基)庚酸酯作为从秀丽隐杆线虫中分离出的信息素的合成和抗衰老和压力相关的效应。使用与衰老、压力、代谢、体内信号传递系统以及抗癌、肥胖和抑制衰老和压力的药物相关的信息素，可以开发医用物质。
• A crystalline furanose derivative of ascarylose. Synthesis of 2,5-di-O-benzoyl-3,6-dideoxy-α-L-arabino-hexofuranose
  作者：Oscar J. Varela、Alicia Fernández Cirelli、Rosa M. de Lederkremer

  DOI：10.1016/s0008-6215(00)84569-3

  日期：1980.10