methyl 6-C-(2,6-anhydro-1-deoxy-D-glycero-L-manno-heptitol-1-yl)-6-deoxy-α-D-glucopyranoside | 175272-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-C-(2,6-anhydro-1-deoxy-D-glycero-L-manno-heptitol-1-yl)-6-deoxy-α-D-glucopyranoside
• 英文别名: (2R,3R,4R,5R,6S)-2-(hydroxymethyl)-6-[2-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]ethyl]oxane-3,4,5-triol
• CAS: 175272-03-4
• 化学式: C₁₄H₂₆O₁₀
• 分子量: 354.354
• InChiKey: NZZFEUNDIKEEJZ-BRPLAWHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6-C-(2,6-anhydro-1-deoxy-D-glycero-L-manno-heptitol-1-yl)-6-deoxy-α-D-glucopyranoside 以 吡啶 为溶剂， 以70%的产率得到Acetic acid (2R,3S,4R,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2-((2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of α- and β-d-(1→6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes

  摘要：

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.

  DOI：

  10.1021/jo971177n
• 作为产物：
  描述：

  methyl 6-C-(2,6-anhydro-1-deoxy-1-dehydro-3,4,5,7-tetra-O-benzyl-D-glycero-L-manno-heptitol-1-yl)-6-deoxy-6-dehydro-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 氨 、 sodium acetate 、 sodium 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.25h， 生成 methyl 6-C-(2,6-anhydro-1-deoxy-D-glycero-L-manno-heptitol-1-yl)-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  C-Glycosyl Aldehydes:  Synthons for C-Linked Disaccharides

  摘要：

  DOI：

  10.1021/jo9517095

文献信息

• <i>C</i>-Glycosyl Aldehydes:  Synthons for <i>C</i>-Linked Disaccharides
  作者：William R. Kobertz、Carolyn R. Bertozzi、Mark D. Bednarski

  DOI：10.1021/jo9517095

  日期：1996.1.1
• Synthesis of α- and β-<scp>d</scp>-(1→6)-<i>C</i>-Disaccharides by Wittig Olefination of Formyl <i>C</i>-Glycosides with Glycopyranose 6-Phosphoranes
  作者：Alessandro Dondoni、Helene M. Zuurmond、Alessia Boscarato

  DOI：10.1021/jo971177n

  日期：1997.11.1

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.