(2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate | 1072440-22-2

• 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: (2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate
• 英文别名: methyl (Z,2S,6S,7R,8R,9R)-6,9-dihydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-7,8,10-tris(phenylmethoxy)dec-4-enoate
• CAS: 1072440-22-2
• 化学式: C₃₇H₄₇NO₉
• 分子量: 649.781
• InChiKey: NKVFPJGQOXHLMU-KGSOFJSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  47
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate 在 sodium tetrahydroborate 、 mercury(II) trifluoroacetate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (S)-methyl 4-((2S,3S,4R,5R,6R)-4,5-di(benzyloxy)-6-((benzyloxy)-methyl)-3-hydroxytetrahydro-2H-pyran-2yl)-2-((tert-butoxycarbonyl)amino)butanoate
  参考文献：
  名称：

  Synthesis of β-C-GlcNAc Ser from β-C-Glc Ser

  摘要：

  The glycosylation of proteins, specifically installation of O-GlcNAc on Ser/Thr residues, is a dynamic control element for transcription repression, protein degradation, and nutrient sensing. To provide homogeneous and stable structures with this motif, the synthesis of a C-linked mimic, C-GlcNAc Ser, has been prepared from the C-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The C-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route.

  DOI：

  10.1021/jo401044x
• 作为产物：
  描述：

  甲醇 、 tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate 在 potassium carbonate 作用下， 反应 1.5h， 以92%的产率得到(2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate
  参考文献：
  名称：

  由常见中间体合成α-和β-C-吡喃葡萄糖基丝氨酸。

  摘要：

  从通用的高级合成中间体中可以得到导致C连接的α-或β-吡喃葡萄糖基丝氨酸的通用合成方法。倒数第二个甲醇在烯烃上的环化和内酯的甲醇分解选择性地产生α-键。这些最后步骤的转座选择性地导致β-连接的异构体。

  DOI：

  10.1021/ol802009v

文献信息

• Syntheses of α- and β-C-Glucopyranosyl Serines from a Common Intermediate
  作者：Ernest G. Nolen、Laurence A. Donahue、Rebecca Greaves、Trevor A. Daly、David R. Calabrese

  DOI：10.1021/ol802009v

  日期：2008.11.6

  A versatile synthesis leading to either C-linked alpha- or beta-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the alpha-linkage. A transposition of these last steps leads to the beta-linked isomer selectively.

  从通用的高级合成中间体中可以得到导致C连接的α-或β-吡喃葡萄糖基丝氨酸的通用合成方法。倒数第二个甲醇在烯烃上的环化和内酯的甲醇分解选择性地产生α-键。这些最后步骤的转座选择性地导致β-连接的异构体。
• Synthesis of β-<i>C</i>-GlcNAc Ser from β-<i>C</i>-Glc Ser
  作者：Ernest G. Nolen、Leyan Li、Kristopher V. Waynant

  DOI：10.1021/jo401044x

  日期：2013.7.5

  The glycosylation of proteins, specifically installation of O-GlcNAc on Ser/Thr residues, is a dynamic control element for transcription repression, protein degradation, and nutrient sensing. To provide homogeneous and stable structures with this motif, the synthesis of a C-linked mimic, C-GlcNAc Ser, has been prepared from the C-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The C-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route.