methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-gluco-hepto-1,7-dialdopyranoside | 174155-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-gluco-hepto-1,7-dialdopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzyl-α-D-exodialdo-1,6-pyranoside；2-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]acetaldehyde
• CAS: 174155-13-6
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: YTXMMTWKVSJBCI-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-gluco-hepto-1,7-dialdopyranoside 在 吡啶 、 sodium tetrahydroborate 、 copper(II) sulfate 、 D-脯氨酸 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.08h， 生成 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside
  参考文献：
  名称：

  General Homologation Strategy for Synthesis of l-glycero- and d-glycero-Heptopyranoses

  摘要：

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

  DOI：

  10.1021/acs.orglett.5b02620
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-α-D-glucopyranoside 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-gluco-hepto-1,7-dialdopyranoside
  参考文献：
  名称：

  α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase

  摘要：

  Glucose-6-phosphatase (G6Pase) is an essential metabolic enzyme that has upregulated activity in Type II diabetes. Synthetic analogs of the G6Pase substrate, glucose-6-phosphate (G6P), may provide new tools to probe enzyme activity, or lead to specific inhibitors of glycosylphosphatase enzymes. Here we have developed synthetic routes to a panel of non-hydrolyzable G6P analogs containing alpha-bromo,alpha,alpha-dibromo, and alpha-bromo-alpha, beta-unsaturated phosphonates compatible with a carbohydrate nucleus. We confirm that these functionalities have potency as inhibitors of G6Pase in vitro, providing a series of new phosphate isosteres that can be exploited for inhibitor design. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.003

文献信息

• Synthesis of glycosyl chlorides with acid-labile protecting groups
  作者：Shang-Cheng Hung、Chi-Huey Wong

  DOI：10.1016/0040-4039(96)01006-4

  日期：1996.7

  Glycosyl chlorides with acid-labile protecting groups were prepared from their corresponding alcohols under basic conditions in good yields. The synthesis of a 1,6-C-linked disaccharide was carried out via reaction of a glycosyl chloride with an aldehyde in the presence of samarium(II) diiodide.

  在碱性条件下，由其相应的醇以良好的收率制备了具有酸不稳定保护基的糖基氯。在二碘化sa（II）存在下，通过糖基氯与醛的反应进行1，6-C-连接的二糖的合成。
• Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides
  作者：Paolo Ronchi、Stefano Vignando、Sara Guglieri、Laura Polito、Luigi Lay

  DOI：10.1039/b822989a

  日期：——

  An approach to the synthesis of pseudo-oligosaccharides based on the cross-metathesis reaction between distinct sugar-olefins, followed by intramolecular cyclization of the obtained heterodimer, is presented. In particular, the relative efficiency of two alternative approaches, the straightforward cross-metathesis reaction and the two-step procedure (self-metathesis followed by cross- metathesis), was explored and compared for diverse sugar-olefin substrates. Some representative examples of intramolecular cyclization using iodine as an electrophilic promoter, are also reported.

  本文提出了一种基于不同糖烯之间的交叉易位反应，随后通过所得异二聚体的分子内环化来合成伪寡糖的方法。特别是，针对多种糖烯底物，探究并比较了两种替代方法的相对效率：直接的交叉易位反应和两步程序（自我易位后进行交叉易位）。此外，还报告了一些使用碘作为亲电促进剂的分子内环化的代表性实例。
• Stereoselective Synthesis of <i>α</i>-<i>C</i>-Glucosamines via Anomeric Organosamarium Reagents
  作者：Lise Andersen、Lise Munch Mikkelsen、Jean-Marie Beau、Troels Skrydstrup

  DOI：10.1055/s-1998-1944

  日期：1998.12

  The direct coupling of the pyridyl sulfone of N-acetylglucosamine with aldehydes or ketones is promoted by samarium diiodide affording the corresponding α-C-glycosides preferentially. A C-disaccharide has been synthesized using this approach.

  N-乙酰氨基葡萄糖的吡啶磺酸酯与醛或酮的直接耦合在二碘化钐的促进下优先生成相应的α-C-糖苷。使用这种方法合成了C-双糖。
• 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.
• Hung, Shang-Cheng; Wong, Chi-Huey, Angewandte Chemie, 1996, vol. 108, # 22, p. 2829 - 2832
  作者：Hung, Shang-Cheng、Wong, Chi-Huey

  DOI：——

  日期：——