α-methyl-6-O-(dihydroxyphosphoryl)-D-glucopyranoside | 15416-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-methyl-6-O-(dihydroxyphosphoryl)-D-glucopyranoside
• 英文别名: glucose-1-O-methyl-6-phospahte；methyl-(O⁶-phosphono-α-D-glucopyranoside)；Methyl-(O⁶-phosphono-α-D-glucopyranosid)；Methyl-<α-D-glucopyranosid-6-dihydrogenphosphat>；Methyl-α-D-glukopyranosid-6-phosphat；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 15416-98-5
• 化学式: C₇H₁₅O₉P
• 分子量: 274.164
• InChiKey: RXYNVAYAPLNZFK-ZFYZTMLRSA-N

物化性质

• 沸点：
  537.3±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  α-methyl-6-O-(dihydroxyphosphoryl)-D-glucopyranoside 在 (2,9-dimethyl-1,10-phenanthroline)Pd(acetonitrile)2(OTf)2 、 叔丁基对苯醌 作用下， 以 氘代二甲亚砜 、 苯 为溶剂， 生成 methyl 3-keto-6-phospho-α-glucose
  参考文献：
  名称：

  未保护的氨基糖苷和糖磷酸盐的位点选择性钯催化氧化

  摘要：

  氨基糖苷和糖磷酸盐中的氨基和磷酸盐的质子化允许直接钯催化的位点选择性氧化，而无需使用保护基团。卡那霉素和阿米卡星的位点选择性氧化可以制备一组 3'-修饰的氨基糖苷衍生物，其中两种衍生物对抗生素耐药性大肠杆菌菌株显示出良好的活性。

  DOI：

  10.1002/chem.202400017
• 作为产物：
  描述：

  在 碘代三甲硅烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以88%的产率得到α-methyl-6-O-(dihydroxyphosphoryl)-D-glucopyranoside
  参考文献：
  名称：

  磷酸迁移酯交换的控制允许区域选择性地获得糖磷酸盐

  摘要：

  多羟基化体系中的磷酸酯通常会在各种反应条件下因不受控制的迁移而受损。氟化铯被证明是一种试剂，可在酯交换过程中控制伯磷酸盐的迁移。这允许轻松交换磷酸保护基团，从而增强合成战略灵活性和区域选择性磷酸盐安装。机理分析表明，氟化物诱导的扩展溶剂球调节磷的空间体积以有利于主要位置。

  DOI：

  10.1021/ol303271z

文献信息

• Inositol Biotransformation
  申请人：UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS

  公开号：US20160168607A1

  公开（公告）日：2016-06-16

  Disclosed is a method of preparing pure or substantially pure D-myo-inositol-3-phosphate from glucose-6-phosphate and/or fructose-6-phosphate. The method may also be applied to protected and/or derivative forms of glucose-6-phosphate and/or fructose-6-phosphate so as to form protected/derivative forms of D-myo-inositol-3-phosphate, for use in further chemical reactions. The enzyme D-myo-inositol-3-phosphate synthase (INO1) is contacted with the glucose-6-phosphate and/or fructose-6-phosphate to generate labeled or unlabeled, protected or unprotected D-myo-inositol-3-phosphate, which may be further reacted and/or purified.

  披露了一种从葡萄糖-6-磷酸和/或果糖-6-磷酸制备纯净或基本纯净的D-肌醇-3-磷酸的方法。该方法也可应用于葡萄糖-6-磷酸和/或果糖-6-磷酸的保护形式和/或衍生物形式，以形成D-肌醇-3-磷酸的保护/衍生物形式，用于进一步的化学反应。D-肌醇-3-磷酸合酶（INO1）酶与葡萄糖-6-磷酸和/或果糖-6-磷酸接触，以生成标记的或未标记的、保护的或未保护的D-肌醇-3-磷酸，该磷酸可进一步反应和/或纯化。
• Regioselective Phosphorylation of Carbohydrates and Various Alcohols by Bacterial Acid Phosphatases; Probing the Substrate Specificity of the Enzyme fromShigella flexneri
  作者：Teunie van Herk、Aloysius F. Hartog、Alida M. van der Burg、Ron Wever

  DOI：10.1002/adsc.200505072

  日期：2005.6

  broad range of carbohydrates and alcohols. Many cyclic carbohydrates are phosphorylated in a regioselective manner. Non-cyclic carbohydrates are phosphorylated as well. Phosphorylation of linear alcohols, cyclic and aromatic alcohols is also possible. In all cases the acid phosphatase from Shigella prefers a primary alcohol function above a secondary one. We conclude that these enzymes are an attractive

  细菌非特异性酸性磷酸酶通常催化多种底物的去磷酸化。如前所述，来自弗氏志贺氏菌和肠炎沙门氏菌的酶也能够使用廉价的焦磷酸盐作为磷酸盐供体，催化将肌苷磷酸化为肌苷单磷酸和将D-葡萄糖磷酸化为D-葡萄糖6-磷酸（D-G6P）。经过优化后，在后一反应中可实现高收率（95％），我们在此表明​​可以以制备方式使用这些酶。这促使我们使用31P NMR和HPLC还可以使多种碳水化合物和醇类进行磷酸化。许多环状碳水化合物以区域选择性方式被磷酸化。非环状碳水化合物也被磷酸化。直链醇，环状和芳族醇的磷酸化也是可能的。在所有情况下，志贺氏菌的酸性磷酸酶都比伯醇更喜欢伯醇功能。我们得出结论，在广泛范围的化合物磷酸化中，这些酶是现有化学和酶促方法的一种有吸引力的替代物。
• Levene; Meyer, Journal of Biological Chemistry, 1921, vol. 48, p. 233,243
  作者：Levene、Meyer

  DOI：——

  日期：——
• Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates
  作者：Morten Meldal、Mette Knak Christensen、Klaus Bock

  DOI：10.1016/0008-6215(92)80082-c

  日期：1992.11

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.
• 232. Carbohydrate phosphoric esters. Part I. The alkaline hydrolysis of α-methylglucopyranoside-6-phosphate, methylglucofuranoside-3-phosphates and isopropylidene glucofuranose-3- and -6-phosphates
  作者：E. E. Percival、E. G. V. Percival

  DOI：10.1039/jr9450000874

  日期：——