<1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol | 144811-29-0

• 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: <1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol
• 英文别名: (1R,2R,3S,4R,5S)-2-azido-3,4-bis(methoxymethoxy)-5-phenylmethoxy-1-(phenylmethoxymethyl)cyclopentan-1-ol
• CAS: 144811-29-0
• 化学式: C₂₄H₃₁N₃O₇
• 分子量: 473.526
• InChiKey: ZVZDCOZHHUXCEN-VDLPQLTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  <1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol 在 盐酸 、 lithium aluminium tetrahydride 、 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 29.0h， 生成 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
  参考文献：
  名称：

  Syntheses and absolute configurations of trehazolin and its aglycon

  摘要：

  DOI：

  10.1021/ja00051a051
• 作为产物：
  描述：

  <1R-(1α,2α,3β,4α,5α)>-2-(Benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 二乙二醇 为溶剂， 反应 48.0h， 以78%的产率得到<1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol
  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

文献信息

• Synthesis of trehazolin .BETA.-anomer.
  作者：YOSHIYUKI KOBAYASHI、MASAO SHIOZAKI

  DOI：10.7164/antibiotics.47.243

  日期：——

  Synthesis of trehazolin β-anomer (3) from a D-glucose derived azido alcohol (4), was accomplished. 2-Chloro-l-methylpyridinium iodide was used in place of 2-chloro-3-ethylbenzoxazolium tetrafluoroborate as a means of preventing concomitant anomerization. Evaluation of compound (3) reveals that the stereochemistry of the anomeric position is significant for generation of inhibitory activities towards trehalases.

  完成了从D-葡萄糖衍生的叠氮醇（4）合成trehazolin β-anomer（3）的过程。2-氯-l-甲基吡啶鎓碘化物被用来代替2-氯-3-乙基苯并恶唑鎓四氟硼酸盐，作为防止伴随的异构化的手段。对化合物（3）的评估表明，异构体位置的立体化学对于产生对海藻糖酶的抑制活性非常重要。