methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-α-D-glucopyranoside | 639504-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-α-D-glucopyranoside
• 英文别名: methyl 6-cyano-6-deoxy-2,3,4-tri-O-benzyl-α-D-glucopyranoside；2-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]acetonitrile
• CAS: 639504-86-2
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: NDZNJHZIANQKEC-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 咪唑 、 碘 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.25h， 生成 methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-α-D-glucopyranoside
  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

• Radical Decarboxylative Cyanomethylation of Aliphatic Carboxylic Acids and Uronic Acids via Vinyl Azide Cascade Fragmentation
  作者：Linhua Xu、Qishuai Li、Dongwei Li、Xin Zhou、Ni Song、Peng Wang、Ming Li

  DOI：10.1002/cjoc.202200732

  日期：——

  A direct oxidative radical decarboxylative cyanomethylation of carboxylic acids is described using 3-azido-2-methylbut-3-en-2-ol as the carbon-centered radical acceptor. The transformation is applicable to structurally diverse α-amino acids, α-oxy acids, α-keto acids, pentofuranuronic acids, and hexopyranuronic acids. The mechanistic investigations suggest that a radical process is involved in the

  使用 3-azido-2-methylbut-3-en-2-ol 作为以碳为中心的自由基受体，描述了羧酸的直接氧化自由基脱羧氰甲基化。该转化适用于结构多样的α-氨基酸、α-含氧酸、α-酮酸、戊呋喃糖醛酸和己吡喃糖醛酸。机械研究表明，转变涉及一个激进的过程。这项工作为构建具有生物学相关性的β-氨基酸、5-脱氧-己呋喃糖和 6-脱氧-庚糖提供了一种潜在的方法。
• Synthesis of Nitrogen Heterocycles from Methyl α‐ and β‐<scp>d</scp>‐Glucopyranosides
  作者：Maria Teresa Capanema Pedrosa、Rosemeire Brondi Alves、Maria Auxiliadora Fontes Prado、José Dias de Souza Filho、Ricardo José Alves、Norma Beatriz D'Accorso

  DOI：10.1081/car-120025329

  日期：2003.1.10

  Eight nitrogen heterocycles, mono and disubstituted tetrazoles and oxadiazoles, were synthesized from methyl D-glucopyranoside anomers. The monosubstituted tetrazoles resulted from the reaction of 6-cyanoglucopyranoside derivatives with sodium azide. By alkylation of the monosubstituted tetrazoles, the 1,5 and 2,5 disubstituted tetrazoles were obtained. The monosubstituted tetrazoles were reacted with acetic anhydride to give the oxadiazoles.
• α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase
  作者：A. Michael Downey、Christopher W. Cairo

  DOI：10.1016/j.carres.2013.08.003

  日期：2013.11

  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.