(3aR,4R,5S,6S,6aS)-4-(羟基甲基)-2-[[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氨基]-3a,5,6,6a-四氢环戊烯并[d][1,3]恶唑-4,5,6-三醇 | 132729-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3aR,4R,5S,6S,6aS)-4-(羟基甲基)-2-[[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氨基]-3a,5,6,6a-四氢环戊烯并[d][1,3]恶唑-4,5,6-三醇
• 英文名称: (+)-trehazolin
• 英文别名: Trehazolin；trehazolin；(3aR,4R,5S,6S,6aS)-4-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]imino-3a,5,6,6a-tetrahydro-3H-cyclopenta[d][1,3]oxazole-4,5,6-triol
• CAS: 132729-37-4
• 化学式: C₁₃H₂₂N₂O₁₀
• 分子量: 366.325
• InChiKey: NRKVPNOUINUNKY-UXTOMXPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  205
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3aR,4R,5S,6S,6aS)-4-(羟基甲基)-2-[[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氨基]-3a,5,6,6a-四氢环戊烯并[d][1,3]恶唑-4,5,6-三醇 以 吡啶 为溶剂， 生成 N-acetyltrehazolin octaacetate
  参考文献：
  名称：

  海藻糖酶抑制剂海藻灵的生物合成。

  摘要：

  Trehazolin（1）是由Micromonospora coriacea生产的海藻糖酶抑制剂。通过进料多种标记前体的实验研究了1的生物合成。用[1-13C]-和[6-13C] -D-葡萄糖进料的实验表明，葡萄糖残基和1中的环戊烷环部分的碳骨架均源自葡萄糖，并且C-之间形成CC键在环戊烷环形成过程中出现了图1和C-5中的葡萄糖。此外，用[胍基-13C，15N2] -L-精氨酸进行的实验表明，涉及1的氨基恶唑啉部分的两个氮原子和季碳原子源自精氨酸的a基。使用[1-2H]-，[2-2H]-，[4-2H]-，[6,6-2H2]-和[1,2,3,4,5,6,6-2H7 ] -D-葡萄糖以及[1-13C] -D-果糖表明C-1，C-3，

  DOI：

  10.7164/antibiotics.55.263
• 作为产物：
  描述：

  1,6-脱水-β-D-葡萄糖 在 PdOH/C 吡啶 、 三氟化硼乙醚 、 氢气 、 mercury(II) oxide 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 (3aR,4R,5S,6S,6aS)-4-(羟基甲基)-2-[[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氨基]-3a,5,6,6a-四氢环戊烯并[d][1,3]恶唑-4,5,6-三醇
  参考文献：
  名称：

  Total Synthesis of (+)-Trehazolin: Optically Active Spirocycloheptadienes as Useful Precursors for the Synthesis of Amino Cyclopentitols

  摘要：

  DOI：

  10.1021/ja00152a026

文献信息

• Synthesis of Trehazolin from <scp>d</scp>-Glucose
  作者：Arnaud Boiron、Peter Zillig、Dominik Faber、Bernd Giese

  DOI：10.1021/jo980485y

  日期：1998.8.1

  inhibitor of trehalase, an enzyme that cleaves the reserve carbohydrates of many insects. We describe a short and efficient synthesis of trehazolin (2) and trehazolamine (5) that mimics its hypothetical biosynthesis. Starting molecule for the synthesis of trehazolamine (5) is glucose from which three chiral centers are conserved during the reaction sequence. The remaining two chiral centers of trehazolamine

  Trehazolin（2）是海藻糖酶的一种特异抑制剂，海藻糖酶可切割许多昆虫的储备碳水化合物。我们描述了模仿其假设的生物合成的Trehazolin（2）和Trehazolamine（5）的短而有效的合成。合成Trehazolamine（5）的起始分子是葡萄糖，在反应过程中从中保守了三个手性中心。在酮肟醚16的还原环化反应和肟醚18的还原反应中，立体选择性地形成了Trehazolamine（5）的其余两个手性中心。在从15开始的8个步骤中，trehazolamine（5）的总收率为22％。 （2）由海藻胺（5）遵循已知程序，可在3个步骤中达到63％。
• Polyhydroxycyclopentane derivatives, their preparation and their
  申请人：Sankyo Company, Limited

  公开号：US05260447A1

  公开（公告）日：1993-11-09

  5-Amino-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetraol and 2-amino-4-(hydroxymethyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]oxazole-4,5, 6-triol, which have the ability to inhibit the activity of sugar hydrolases, especially .beta.-glucosidase and sucrase and can thus be used for the treatment and prophylaxis of tumorous conditions, AIDS, diabetes and obesity, can be prepared by hydrolysis of trehazolin. 2-Amino-4-(hydroxymethyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]oxazole-4,5, 6-triol can also be prepared by fermentation using newly isolated strains Micromonospora sp. SANK 62390, FERM BP-3521 and Amycolatopsis sp. SANK 60791, FERM BP-3513.

  5-氨基-1-（羟甲基）环戊烷-1,2,3,4-四醇和2-氨基-4-（羟甲基）-3a,5,6,6a-四氢-4H-环戊基[d]噁唑-4,5,6-三醇具有抑制糖水解酶活性的能力，特别是β-葡萄糖苷酶和蔗糖酶，因此可用于治疗和预防肿瘤病、艾滋病、糖尿病和肥胖症，可通过对特利霉素的水解制备。2-氨基-4-（羟甲基）-3a,5,6,6a-四氢-4H-环戊基[d]噁唑-4,5,6-三醇也可以通过使用新分离的菌株微单孢菌sp.SANK 62390、FERM BP-3521和链霉菌sp.SANK 60791、FERM BP-3513进行发酵制备。
• Total Synthesis of Trehalase Inhibitor, Trehazolin
  作者：Seiichiro Ogawa、Chikara Uchida

  DOI：10.1246/cl.1993.173

  日期：1993.1

  The total synthesis of trehalase inhibitor, trehazolin has been accomplished by coupling the optically active aminocyclopentanepentaol with α-d-glucopyranosylisothiocyanate derivative, followed by subsequent oxazoline-ring formation and removal of the protecting groups, thereby confirming its absolute configuration.

  通过将具有光学活性的氨基环戊醇与α-d-吡喃葡萄糖基异硫氰酸酯衍生物偶联，随后形成噁唑啉环并去除保护基团，完成了三卤甲烷酶抑制剂三唑啉的全合成，从而确认了其绝对构型。
• Syntheses of Trehazolin, Trehalamine, and the Aminocyclitol Moiety of Trehazolin: Determination of Absolute Configuration of Trehazolin
  作者：Yoshiyuki Kobayashi、Hideki Miyazaki、Masao Shiozaki

  DOI：10.1021/jo00083a023

  日期：1994.2

  The syntheses and determination of the absolute configurations of trehazolin (1), its aglycon (trehalamine (3)), and its aminocyclitol hexaacetate moiety (5) are described. An important intermediate, optically active epoxide 16 alpha, was obtained from an 11-step synthesis starting from D-glucose. The route has [3+2] cycloaddition and Sharpless epoxidation reactions as the key steps. Trehazolin and trehalamine were subsequently synthesized from 16 alpha, utilizing 2-chloro-3-ethyl-benzoxazolium tetrafluoroborate to construct aminooxazoline frameworks via the carbodiimide derivatives 30 and 27 derived from thioureas 29 and 26, respectively. The absolute configurations of the trehazolin aglycon and aminocyclitol moieties were determined to be [3aR-(3a alpha,4 alpha,5 beta,6 alpha,6a alpha)] and [1R-(1 alpha,2 beta,3 alpha,4 beta,5 beta)], respectively. Alternatively, the synthesis of trehazolin could be completed through nonprotected aminocyclitol 32, which was obtainable from deprotection of compound 5 or degradation of natural trehazolin.
• Syntheses and absolute configurations of trehazolin and its aglycon
  作者：Yoshiyuki Kobayashi、Hideki Miyazaki、Masao Shiozaki

  DOI：10.1021/ja00051a051

  日期：1992.12