(2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol | 3867-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol
• 英文别名: methyl β-D-arabinopyranoside；methyl arabinoside；methyl-α-D-arabinopyranoside；Methyl-α-D-arabinopyranosid；methyl alpha-D-arabinopyranoside；(2S,3S,4R,5R)-2-methoxyoxane-3,4,5-triol
• CAS: 3867-83-2
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: ZBDGHWFPLXXWRD-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol 在 吡啶 、 硫酸 、 copper(II) sulfate 、 丙酮 作用下， 生成 methyl 2-O-methanesulfonyl-α-D-arabinopyranoside
  参考文献：
  名称：

  The Preparation of Crystalline 2-O-Methylsulfonyl-D-arabinose and Some of Its Derivatives

  摘要：

  DOI：

  10.1021/ja01552a056
• 作为产物：
  描述：

  1,3,5-三苯甲酰基-D-呋喃核糖 在 吡啶 、 甲醇 、 二氯甲烷 、 sodium methylate 作用下， 生成 (2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Evidence that the Supposed 3,5-Di-O-benzoyl-1,2-O-(1-hydroxybenzylidene)-α-D- ribose is Actually 1,3,5-Tri-O-benzoyl-α-D-ribose

  摘要：

  DOI：

  10.1021/ja01599a048

文献信息

• Periodate oxidation of methyl glycopyranosides: rate coefficients and relative stabilities of intermediate hemiacetals
  作者：Kjell M. Aalmo、Terence J. Painter

  DOI：10.1016/s0008-6215(00)85230-1

  日期：1981.2

  Abstract For oxidation in aqueous sodium metaperiodate at 20°, rate coefficients describing the decay of intact glycoside ( k G ) and the consumption of periodate ( k P ) were measured for the methyl α- and β-glycopyranosides of d -glucose, d -galactose. d -mannose, d -xylose, and d -(or l -)arabinose, and for methyl α- l -rhamnopyranoside. For glycosides containing a cis -1,2-diol group, k G was four

  摘要为了在20°偏高碘酸钠水溶液中进行氧化，测定了d-葡萄糖，d-葡萄糖的甲基α-和β-吡喃葡萄糖苷的速率系数，该系数描述了完整糖苷（k G）的衰变和高碘酸盐的消耗（k P）。半乳糖。d-甘露糖，d-木糖和d-（或1-）阿拉伯糖，以及对于甲基α-1-r-鼠李糖吡喃糖苷。对于含有顺式-1，2-二醇基团的糖苷，其k G是仅含有反式－1，2-二醇基团的糖苷的四到十六倍。对于异头对，（k G）α/（k G）β在0.6到1.7之间变化。动力学表明，单独氧化的中间体部分以不反应的形式存在，据推测是环状半缩醛。对于六吡喃糖苷而不是对五吡喃糖苷，半缩醛的稳定性（如k P的极限值所示）α比β异头物大得多。从对半缩醛的可能结构和构象的考虑，推断该结果是异头作用的体现。
• GLYCOSIDATION OF SUGARS: II. METHANOLYSIS OF D-XYLOSE, D-ARABINOSE, D-LYXOSE, AND D-RIBOSE
  作者：C. T. Bishop、F. P. Cooper

  DOI：10.1139/v63-405

  日期：1963.11.1

  Rates of methanolysis reactions of D-xylose, D-arabinose, D-lyxose, and D-ribose have been determined. It was found that methanolysis of a pentose proceeds to equilibrium through four distinguishable, competing reactions: (1) pentose → furanosides; (2) anomerization of furanosides; (3) furanosides → pyranosides; (4) anomerization of pyranosides. The glycoside compositions at equilibrium are interpreted in terms of stabilities of each of the four glycosides from each sugar as influenced by steric and ionic effects; a system of conformational analysis of furanoside rings is presented. The free energies of reaction in anomerization of pyranosides were in excellent agreement with values calculated from previously reported interaction energies in the pyranoid ring. The relative rates of the reactions were consistent with the view that non-bonded interactions in the methyl glycosides are relieved in the transition states for their interconversions.

  甲醇解反应的速率确定了D-木糖、D-阿拉伯糖、D-来苏糖和D-核糖的速率。发现戊糖的甲醇解反应通过四个可区分的、竞争性反应达到平衡：(1)戊糖→呋喃糖苷；(2)呋喃糖苷的异构化；(3)呋喃糖苷→吡喃糖苷；(4)吡喃糖苷的异构化。平衡时的糖苷组成是根据每种糖的四种糖苷的稳定性来解释的，这种稳定性受到立体和离子效应的影响；提出了呋喃糖苷环的构象分析方法。吡喃糖苷异构化反应的自由能变化与先前报道的吡喃环相互作用能计算出的值非常一致。这些反应的相对速率与这种观点相符，即在甲基糖苷的过渡态中，非键合相互作用得到了缓解。
• Medicinal Foodstuffs. XVI. Sugar Beet. (3). Absolute Stereostructures of Betavulgarosides II and IV, Hypoglycemic Saponins Having a Unique Substituent, from the Roots of Beta vulgaris L.
  作者：Toshiyuki MURAKAMI、Hisashi MATSUDA、Masahiro INADZUKI、Kazuhiro HIRANO、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.47.1717

  日期：——

  The absolute stereostructures of betavulgaroside II having a dioxolane-type substituent and betavulgaroside IV having an acetal-type substituent, which were isolated from the roots of Beta vulgaris L. (sugar beet, Chenopodiaceae) and exhibited hypoglycemic activity on glucose-loaded rats, were determined by the chemical correlations of betavulgarosides II and IV with a known saponin, momordin I. In these chemical correlations, the α-L-arabinopyranosyl moiety of momordin I was converted to a dioxolane-type substituent of betavulgaroside II or to an acetal-type substituent of betavulgaroside IV. Additionally, the 2'-diastereoisomer of betavulgaroside IV was synthesized from momordin I, and four acetal-type substituent analogues were also synthesized from L- and D-arabinose.

  通过将已知皂苷 momordin I 与 betavulgaroside II 和 IV 进行化学关联，确定了从甜菜（藜科）根部分离出的具有对葡萄糖负荷大鼠的降血糖活性的含有二氧六环型取代基的 betavulgaroside II 和含有缩酮型取代基的 betavulgaroside IV 的绝对立体结构。在这些化学关联中，momordin I 的 α-L-阿拉伯糖苷部分被转化为 betavulgaroside II 的二氧六环型取代基或 betavulgaroside IV 的缩酮型取代基。此外，从 momordin I 合成了 betavulgaroside IV 的 2'-非对映异构体，并从 L- 和 D-阿拉伯糖合成了四种缩酮型取代基类似物。
• Absolute Stereostructures of Betavulgarosides III and IV, Inhibitors of Glucose Absorption, from the Roots of Beta vulgaris L.(Sugar Beet).
  作者：Masayuki YOSHIKAWA、Toshiyuki MURAKAMI、Masahiro INADUKI、Kazuhiro HIRANO、Johji YAMAHARA、Hisashi MATSUDA

  DOI：10.1248/cpb.45.561

  日期：——

  The absolute stereostructures of betavulgarosides III and IV, which were isolated from the roots of Beta vulgaris L. (sugar beet) and exhibited inhibitory activity on glucose absorption, were determined by the chemical correlation of betavulgaroside IV with a known saponin momordin I, which included the conversion from the α-L-arabinopyranosyl moiety of momordin I to the acidic acetal-type substituent of betavulgarosides III and IV via the α-L-ribopyranosyl derivative. Furthermore, four acidic acetal-type substituent analogues were synthesized from L- and D-arabinose.

  从甜菜（Beta vulgaris L.）的根部分离得到了具有抑制葡萄糖吸收活性的β甜菜苷III和IV，并通过β甜菜苷IV与已知的皂苷momordin I的化学相关性确定了它们的绝对立体结构。这一过程包括将momordin I中的α-L-阿拉伯呋喃糖基部分转化为β甜菜苷III和IV中的酸性缩醛型取代基，即α-L-核呋喃糖衍生物。此外，还从L-和D-阿拉伯糖合成了四种酸性缩醛型取代基类似物。
• 2'-deoxy-L-nucleosides
  申请人：Watanabe Kyoichi

  公开号：US20050090660A1

  公开（公告）日：2005-04-28

  This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH 2 , NHR′, or NR′R″ Z is H, F, Cl, Br, I, CN, or NH 2 . R is hydrogen, halogen, lower alkyl of C 1 -C 6 or aralkyl, NO 2 , NH 2 , NHR′, NR′R″, OH, OR, SH, SR, CN, CONH 2 , CSNH 2 , CO 2 H, CO 2 R′, CH 2 CO 2 H, CH 2 CO 2 R′, CH═CHR, CH 2 CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C 1 -C 6 . R 13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

  这项发明提供了制备具有以下结构的化合物的方法： 其中 X和Y相同或不同，且H、OH、OR、SH、SR、NH2、NHR′或NR′R″ Z为H、F、Cl、Br、I、CN或NH2 R为氢、卤素、C1-C6的低碳烷基或芳基烷基、NO2、NH2、NHR′、NR′R″、OH、OR、SH、SR、CN、CONH2、CSNH2、CO2H、CO2R′、CH2CO2H、CH2CO2R′、CH═CHR、CH2CH═CHR或C═CR。 R′和R″相同或不同，且为C1-C6的低碳烷基。 R13为氢、烷基、酰基、磷酸酯（单磷酸酯、二磷酸酯、三磷酸酯或稳定磷酸酯）或硅基。