N-acetyltrehazolamine pentaacetate | 149091-75-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyltrehazolamine pentaacetate
• 英文别名: <1R-(1α,2β,3α,4β,5β)>-5-Acetamido-1,2,3,4-tetraacetoxy-1-(acetoxymethyl)cyclopentane；<1R-(1α,2β,3α,4β,5β)>-5-acetamide-1-acetoxymethyl-1,2,3,4-tetraacetoxycyclopentane；[1R-(1α,2β,3α,4β,5β)]-5-acetamido-1,2,3,4-tetraacetoxy-1-(acetoxymethyl)cyclopentane；[(1R,2R,3S,4R,5S)-2-acetamido-1,3,4,5-tetraacetyloxycyclopentyl]methyl acetate
• CAS: 149091-75-8
• 化学式: C₁₈H₂₅NO₁₁
• 分子量: 431.397
• InChiKey: VVQDCLCCQCLPAL-DZVNLGKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-acetyltrehazolamine pentaacetate 在 盐酸 作用下， 反应 2.0h， 以89%的产率得到DL-(1,3/2,4,5)-5-amino-1-C-(hydroxymethyl)cyclopentane-1,2,3,4-tetraol
  参考文献：
  名称：

  Syntheses of Trehazolin, Trehalamine, and the Aminocyclitol Moiety of Trehazolin: Determination of Absolute Configuration of Trehazolin

  摘要：

  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.

  DOI：

  10.1021/jo00083a023
• 作为产物：
  描述：

  (3aR,6S,6aS)-2,2-dimethyl-4-(phenylmethoxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-ol 在 palladium on activated charcoal 吡啶 、 sodium benzoate 、 4-二甲氨基吡啶 、 氢氧化钾 、 ammonium cerium(IV) nitrate 、 三氟过氧乙酸 、 硫酸 、 水 、 氢气 、 碘 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 、 sodium sulfite 、 锌 、 偶氮二甲酸二乙酯 、 碘甲烷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 24.0h， 生成 N-acetyltrehazolamine pentaacetate
  参考文献：
  名称：

  Knapp; Purandare; Rupitz, Journal of the American Chemical Society, 1994, vol. 116, # 16, p. 7461 - 7462

  摘要：

  DOI：

文献信息

• Formal Total Synthesis of (+)-Trehazolin. Application of an Asymmetric Aldol−Olefin Metathesis Approach to the Synthesis of Functionalized Cyclopentenes
  作者：Michael T. Crimmins、Elie A. Tabet

  DOI：10.1021/jo015568k

  日期：2001.6.1

  An asymmetric synthesis of the aminocyclopentitol pseudosugar of trehazolin has been completed. The synthesis hinges on an asymmetric aldol-ring closing metathesis strategy to construct the five-membered ring with control of both the relative and absolute stereochemistry.

  trehazolin的氨基环戊醇假糖的不对称合成已经完成。该合成取决于不对称的醛醇环闭合复分解策略，以在相对和绝对立体化学的控制下构建五元环。
• Stereocontrolled synthesis of the aminocyclitol moiety of (+)-trehazolin via C–H insertion reaction of alkylidenecarbene
  作者：Megumi Akiyama、Toshiki Awamura、Kazuhito Kimura、Yoshimi Hosomi、Ayako Kobayashi、Kazutaka Tsuji、Atsuhito Kuboki、Susumu Ohira

  DOI：10.1016/j.tetlet.2004.07.087

  日期：2004.9

  The aminocyclitol moiety of (+)-trehazolin, a powerful trehalase inhibitor, was synthesized in a stereocontrolled manner from cis-2-butene-1,4-diol via C–H insertion reaction of the alkylidenecarbene, followed by regioselective opening of the epoxide ring. It was obtained in an enantiomerically pure form by twice using Sharpless asymmetric epoxidation.

  （+）-trehazolin的氨基环糖醇部分（一种强大的海藻糖酶抑制剂）是通过顺式-2-丁烯-1,4-二醇通过亚烷基卡宾的CH插入反应以立体控制方式合成的，然后进行环氧化物的区域选择性开放戒指。通过两次使用Sharpless不对称环氧化，以对映体纯的形式获得它。
• Synthesis and absolute configuration of trehazolin aminocyclitol moiety
  作者：Yoshiyuki Kobayashi、Hideki Miyazaki、Masao Shiozaki

  DOI：10.1016/s0040-4039(00)60330-1

  日期：1993.2

  2β,3α,4β,5β)]-5-acetamide-1-acetoxymethyl-1,2,3,4-tetraacetoxycyclopentane 2 was synthesized from D-glucose. Compound 2 was identical in all respects with the hexaacetate derived from the natural trehazolin aminocyclitol moiety.

  由D-葡萄糖合成旋光的[1 R-（1α，2β，3α，4β，5β）]-5-乙酰胺-1-乙酰氧基甲基-1,2,3,4-四乙酰氧基环戊烷2。化合物2在所有方面都与衍生自天然trehazolin氨基环糖醇部分的六乙酸酯相同。
• Stereoselective synthesis of aminocyclitol moieties of trehazolin and trehalostatin via enyne metathesis protocol
  作者：Palakodety Radha Krishna、Munagala Alivelu

  DOI：10.1016/j.tetlet.2010.09.084

  日期：2010.12

  Stereoselective and efficient synthesis of respective aminocyclitol moieties 1a and 2a of trehazolin and trehalostatin as hexaacetates 1b and 2b using ring-closing enyne metathesis as the key reaction is described. (C) 2010 Elsevier Ltd. All rights reserved.