methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside | 139242-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-[2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl]oxane
• CAS: 139242-12-9
• 化学式: C₆₃H₆₈O₁₀
• 分子量: 985.227
• InChiKey: KQHUAOQWIMMBJT-RIDXZFEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  73
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硫酸 、 溶剂黄146 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 8.75h， 生成 6,10:13,17-dianhydro-7,8,9,14,15,16,18-hepta-O-benzyl-2,3,4,5,11,12-hexadeoxy-1-O,2-N-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-allo-L-gulo-octadec-3-enitol
  参考文献：
  名称：

  链烯基C-糖苷-乙烯基恶唑烷交叉复分解的简明C-糖基氨基酸合成。糖基丝氨酸，天冬酰胺和羟基降缬氨酸等位基因的合成

  摘要：

  已经开发出收敛合成以通过以下方式提供C-连接的糖基氨基酸：交叉复分解 的 乙烯基塑料， 烯丙基和丁烯基C-糖苷与N -Boc-乙烯基恶唑烷 使用Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylideneruthenium 卡宾。该方法已被用于通过α-连接在β- D - C-龙胆二糖的异头碳处引入α-氨基戊酸链，以得到α的完全人工糖基α-氨基酸。二糖。该化合物代表天然糖肽肾上腺皮质激素的α-连接的糖基天冬酰胺部分的等排体。

  DOI：

  10.1039/b106029p
• 作为产物：
  描述：

  (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)ethynyl)tetrahydro-2H-pyran 在 Lindlar's catalyst 喹啉 、 氢气 、 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 24.33h， 生成 methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside
  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

文献信息

• Novel Carboranyl C-Glycosides for the Treatment of Cancer by Boron Neutron Capture Therapy
  作者：Lutz F. Tietze、Ulrich Griesbach、Ingrid Schuberth、Ulrich Bothe、Alberto Marra、Alessandro Dondoni

  DOI：10.1002/chem.200390148

  日期：2003.3.17

  The synthesis of the novel unprotected carboranyl C-glycosides 2 and 20-24 starting from ethynyl C-glycosides 1, 5-8, 10, and 13 is described. The new compounds are highly water-soluble and display only a very low cytotoxicity, which makes them promising candidates for use in boron neutron capture therapy for the treatment of cancer.

  描述了从乙炔基C-糖苷1、5-8、10和13开始的新型未保护的碳硼烷基C-糖苷2和20-24的合成。这些新化合物高度水溶性，并且仅显示出非常低的细胞毒性，这使其成为有望用于硼中子俘获疗法以治疗癌症的候选药物。
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• A concise C-glycosyl amino acid synthesis by alkenyl C-glycoside–vinyloxazolidine cross-metathesis. Synthesis of glycosyl serine, asparagine and hydroxynorvaline isosteres
  作者：Alessandro Dondoni、Pier Paolo Giovannini、Alberto Marra

  DOI：10.1039/b106029p

  日期：——

  A convergent synthesis has been developed to afford C-linked glycosyl amino acids by cross-metathesis of vinyl, allyl, and butenyl C-glycosides with N-Boc-vinyloxazolidine using the Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylideneruthenium carbene. The method has been employed to introduce through an α-linkage, an α-aminopentanoic acid chain at the anomeric carbon of β-D-C-gentiobiose to give a totally

  已经开发出收敛合成以通过以下方式提供C-连接的糖基氨基酸：交叉复分解 的 乙烯基塑料， 烯丙基和丁烯基C-糖苷与N -Boc-乙烯基恶唑烷 使用Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylideneruthenium 卡宾。该方法已被用于通过α-连接在β- D - C-龙胆二糖的异头碳处引入α-氨基戊酸链，以得到α的完全人工糖基α-氨基酸。二糖。该化合物代表天然糖肽肾上腺皮质激素的α-连接的糖基天冬酰胺部分的等排体。
• 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.