(Z)-methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside | 139195-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-[(Z)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethenyl]oxane
• CAS: 139195-45-2
• 化学式: C₆₃H₆₆O₁₀
• 分子量: 983.211
• InChiKey: YYNSDWPBZWHYGV-NZTPLXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  73
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside 在 sodium hydroxide 、 borane-d3-tetrahydrofuran 、 双氧水 作用下， 生成 (1S,2R)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)ethan-2-d-1-ol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 7. Preferred conformation of carbon analogs of isomaltose and gentiobiose

  摘要：

  The preferred solution conformation of the 1,6-linked C-disaccharides 3 and 4, carbon analogues of methyl isomaltoside and methyl gentiobioside, was shown to be 3-A and 4-A, respectively, by H-1 NMR spectroscopy.

  DOI：

  10.1021/jo00022a039
• 作为产物：
  描述：

  methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 75.0h， 生成 (Z)-methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside
  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

文献信息

• A Ramberg−Bäcklund Approach to the Synthesis ofC-Glycosides,C-Linked Disaccharides, andC-Glycosyl Amino Acids
  作者：Duncan E. Paterson、Frank K. Griffin、Marie-Lyne Alcaraz、Richard J. K. Taylor

  DOI：10.1002/1099-0690(200204)2002:7<1323::aid-ejoc1323>3.0.co;2-8

  日期：2002.4

  dioxides using the Meyers variant of the Ramberg−Backlund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg−Backlund rearrangement is also reported. (© Wiley-VCH Verlag GmbH, 69451 Weinheim

  描述了使用 Ramberg-Backlund 重排的 Meyers 变体衍生自 S-糖苷二氧化物的外糖的合成应用。其中包括 β-糖苷酶抑制剂 12 的正式合成和生成螺环葡萄糖衍生物 17 和 18 的有效途径。 使用 Ramberg-Backlund 合成 C-连接的二糖 24、31 和 38 和 C-糖基氨基酸 49重排也有报道。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• 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.
• Preferred conformation of C-glycosides. 7. Preferred conformation of carbon analogs of isomaltose and gentiobiose
  作者：Peter G. Goekjian、Tse Chong Wu、Han Young Kang、Yoshito Kishi

  DOI：10.1021/jo00022a039

  日期：1991.10

  The preferred solution conformation of the 1,6-linked C-disaccharides 3 and 4, carbon analogues of methyl isomaltoside and methyl gentiobioside, was shown to be 3-A and 4-A, respectively, by H-1 NMR spectroscopy.