C-(4,6-O-benzylidene-β-D-glucopyranosyl) methylamine | 136738-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(4,6-O-benzylidene-β-D-glucopyranosyl) methylamine
• 英文别名: Amino(4,6-O-benzylidene-β-D-glucopyranosyl)methane
• CAS: 136738-62-0
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: CJIAZSXUTYRBIX-XADZXUCXSA-N

物化性质

• 熔点：
  230-232 °C (decomp)
• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.17
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  C-(4,6-O-benzylidene-β-D-glucopyranosyl) methylamine 在 吡啶 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 120.0h， 生成 Acetamido(2,3-anhydro-4,6-O-benzylidene-β-D-mannopyranosyl)methane
  参考文献：
  名称：

  C-Glycoside Syntheses. 3. Diastereo-diversified C-Glycosides from D-Glucose

  摘要：

  beta-C-Glycosides with the D-manno, D-allo, and D-altro configurations can be easily obtained by anchimerically assisted inversions, starting from a common beta-C-glycoside precursor, nitro(4,6-O-benzylidene-beta-D-glucopyranosyl)methane (2), which is easily accessible from D-glucose. The observed neighboring group reactions show some similarities to reactions Previously observed for analogous O-glycosides, but also some significant differences due to the acetamidomethyl beta-C-glycoside group, which is present in most of the compounds. The configurations and conformations of all compounds have been comprehensively studied by NMR methods. The result is a viable and extendable synthetic paradigm for the rational synthesis of a wide variety of unusual C-glycoside derivatives, potentially useful for biochemical studies.

  DOI：

  10.1021/jo00110a024
• 作为产物：
  描述：

  D-葡萄糖 在 palladium 10% on activated carbon 、 甲酸铵 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 C-(4,6-O-benzylidene-β-D-glucopyranosyl) methylamine
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides

  摘要：

  A series of N-substituted 1-aminomethyl-beta-D-glucopyranoside derivatives was prepared. These novel synthetic compounds were assessed in vitro for inhibitory activity against yeast a-glucosidase and both rat intestinal a-glucosidases maltase and sucrase. Most of the compounds displayed a-glucosidase inhibitory activity, with IC50 values covering the wide range from 2.3 mu M to 2.0 mM. Compounds 19a (IC50 = 2.31 mu M) and 19b (IC50 = 5.6 mu M) were identified as the most potent inhibitors for yeast a-glucosidase, while compounds 16 (IC50 = 7.7 and 15.6 mu M) and 19e (IC50 = 5.1 and 10.4 mu M) were the strongest inhibitors of rat intestinal maltase and sucrase. Analysis of the kinetics of enzyme inhibition indicated that 19e inhibited maltase and sucrase in a competitive manner. The results suggest that the aminomethyl-beta-o-glucopyranoside moiety can mimic the substrates of a-glucosidase in the enzyme catalytic site, leading to competitive enzyme inhibition. Moreover, the nature of the N-substituent has considerable influence on inhibitory potency. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.002

文献信息

• Phototransamidation as a Method for the Synthesis of<i>N</i>-Glycosyl Asparagines
  作者：Kristóf Vízvárdi、Christian Kreutz、Alexander S. Davis、Vincent P. Lee、Benjamin J. Philmus、Ondrej Simo、Katja Michael

  DOI：10.1246/cl.2003.348

  日期：2003.4

  N-Glycosyl asparagines were synthesized by a mild photochemical coupling method in which a photoreactive amide of an aspartic acid’s β-carboxyl group is condensed with an aminosaccharide. Upon excitation, the γ-carbon becomes susceptible to nucleophilic attack and the obtained N-glycosyl asparagines, which may be useful building blocks for the synthesis of N-glycopeptides and neoglycopeptides, are generated in good yields.

  N-糖苷天冬氨酸是通过一种温和的光化学耦合方法合成的，该方法中，天冬氨酸的β-羧基的光反应酰胺与氨基糖发生缩合。在激发后，γ-碳变得易于受到亲核攻击，所得的N-糖苷天冬氨酸可以作为合成N-糖肽和新糖肽的有用构件，并且产率良好。
• Selective Reductions of <i>C</i>‐(4,6‐<i>O</i>‐Benzylidene‐β‐<scp>d</scp>‐glucopyranosyl) Nitromethane
  作者：Ondrej Simo、Katja Michael、Wesley Yoshida、Vyacheslav A. Chertkov、Paul H. Gross

  DOI：10.1081/scc-200061554

  日期：2005.6.1

  The nitromethyl group of C-(4,6-O-benzylidene-beta-D-glucopyranosyl) nitromethane was manipulated by various reduction and oxidation methods and further functionalizations into -CH2NHOH, -CH=NOH, -CN, -CH=O, and -CH2NHCONH2, all with retention of the 4,6-O-benzylidene group. Certain reduction methods gave rise to a novel secondary amine via an unusual dimeric aminal.