Methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside | 107032-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2-[[(2S,3S,4S,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 107032-98-4
• 化学式: C₁₄H₂₆O₁₀
• 分子量: 354.354
• InChiKey: DVUBRIJBGLANPZ-GTOARBIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 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 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside 在 吡啶 作用下， 反应 12.0h， 以78%的产率得到Methyl 2,3,6-tri-O-acetyl-4-C-(2,6-anhydro-3,4,5,7-tetra-O-acetyl-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Khan, Abu T.; Sharma, Parijat; Schmidt, Richard R., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 9, p. 1353 - 1368

  摘要：

  DOI：
• 作为产物：
  描述：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 在 palladium on activated charcoal 、 bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum 、 lead(II) chloride 4-二甲氨基吡啶 、 四甲基乙二胺 、 氢气 、 四氯化钛 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 反应 30.0h， 生成 Methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-C-Disaccharides¹

  摘要：

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo030039x

文献信息

• A Unified Approach to Differentially Linked β-<i>C</i>-Disaccharides by Ring-Closing Metathesis
  作者：Lei Liu、Maarten H. D. Postema

  DOI：10.1021/ja010641+

  日期：2001.9.1
• Preferred conformation of C-glycosides. 8. Synthesis of 1,4-linked carbon disaccharides
  作者：Yuan Wang、Stefan A. Babirad、Yoshito Kishi

  DOI：10.1021/jo00028a017

  日期：1992.1
• Synthesis of C-disaccharides
  作者：Stefan A. Babirad、Yuan Wang、Yoshito Kishi

  DOI：10.1021/jo00383a045

  日期：1987.4
• Selective radical synthesis of β- C -disaccharides
  作者：Boris Vauzeilles、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(01)01533-7

  日期：2001.10

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.