N'-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N-<<1R-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea | 147237-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N-<<1R-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea
• 英文别名: N-(2,3,4,6,-tetra-O-benzyl-α-D-glucopyranosyl)-N'-<(1R)-2,3,4,5-tetrahydroxy-5-C-(hydroxymethyl)cyclopentyl>thiourea；1-[(1R,2R,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]thiourea
• CAS: 147237-44-3
• 化学式: C₄₁H₄₈N₂O₁₀S
• 分子量: 760.906
• InChiKey: OPQLCFYUIDWZHK-ZQQXOYCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  203
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N'-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N-<<1R-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea 在 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 ((1R,2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-2-hydroxymethyl-cyclopentyl)-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbodiimide
  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：

  (1R,2R,3S,4R,5S)-2-Amino-5-benzyloxy-1-hydroxymethyl-3,4-bis-methoxymethoxy-cyclopentanol 在 palladium dihydroxide 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 85.42h， 生成 N'-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N-<<1R-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea
  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

• 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。
• Uchida, Chikara; Yamagishi, Tatsuya; Ogawa, Seiichiro, Journal of the Chemical Society. Perkin transactions I, 1994, # 5, p. 589 - 602
  作者：Uchida, Chikara、Yamagishi, Tatsuya、Ogawa, Seiichiro

  DOI：——

  日期：——