(5S,6S)-6-methyltetrahydro-2H-pyran-2,5-diol | 51013-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (5S,6S)-6-methyltetrahydro-2H-pyran-2,5-diol
• 英文别名: L-rhodinose；2,3,6-trideoxy-β-threo-hexopyranose；(4S,5S)-4,5-dihydroxy-hexanal (Ξ)-1->5-cyclohemiacetal；ξ-L-threo-2,3,6-trideoxy-hexopyranose；ξ-L-rhodinopyranose；(5S,6S)-6-methyloxane-2,5-diol
• CAS: 51013-33-3；64475-25-8；92583-51-2；95840-34-9；95840-35-0
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: ZCYMCBOUZXAAJG-HVYQYDHPSA-N

物化性质

• 沸点：
  263.6±40.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranoside 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 Amberlyst A 26 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 36.75h， 生成 (5S,6S)-6-methyltetrahydro-2H-pyran-2,5-diol
  参考文献：
  名称：

  Cardillo, Giuliana; Orena, Mario; Sandri, Sergio, Gazzetta Chimica Italiana, 1984, vol. 114, # 7/8, p. 325 - 326

  摘要：

  DOI：

文献信息

• Iridium-Catalyzed Dynamic Kinetic Isomerization: Expedient Synthesis of Carbohydrates from Achmatowicz Rearrangement Products
  作者：Hao-Yuan Wang、Ka Yang、Scott R. Bennett、Sheng-rong Guo、Weiping Tang

  DOI：10.1002/anie.201503151

  日期：2015.7.20

  A highly stereoselective dynamic kinetic isomerization of Achmatowicz rearrangement products was discovered. This new internal redox isomerization provided ready access to key intermediates for the enantio‐ and diastereoselective synthesis of a series of naturally occurring sugars. The nature of the de novo synthesis also enables the preparation of both enantiomers.

  发现了Achmatowicz重排产物的高度立体选择性的动态动力学异构化。这种新的内部氧化还原异构化为一系列天然糖的对映和非对映选择性合成提供了关键中间体的现成通道。从头合成的性质还使得能够制备两种对映异构体。
• Lycoperdinoside A and B, New Glycosides from the Slime Mold Enteridium lycoperdon
  作者：Tomáš Řezanka、Radmila Dvořáková、Lumír O. Hanuš、Valery M. Dembitsky

  DOI：10.1002/ejoc.200300575

  日期：2004.3

  Two, novel, six-membered lactone glycosides (lycoperdinoside A and B) were isolated from the slime mold Enteridium lycoperdon. Their structures, including the absolute configurations of the hydroxy and methyl groups, were determined by means of extensive spectroscopic data such as MS, IR, UV, and 1D and 2D NMR spectra and chemical degradation. The compounds have structures containing a β-L-amiceto

  两种新颖的六元内酯糖苷（番茄红素 A 和 B）从粘液霉菌 Enteridium lycoperdon 中分离出来。它们的结构，包括羟基和甲基的绝对构型，是通过广泛的光谱数据确定的，例如 MS、IR、UV 以及 1D 和 2D NMR 光谱和化学降解。该化合物的结构包含一个β-L-乙酰氨基-(1⇄4)-α-L-乙酰氨基单元和一个β-L-乙酰氨基-(1⇄4)-α-L-乙酰氨基-(1⇄4)-分别为 β-L-紫檀糖基单元。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• The absolute configuration of P-1894B (vineomycin A1), a potent prolyl hydroxylase inhibitor.
  作者：Kazuhiko Ohta、Hisayoshi Okazaki、Toyokazu Kishi

  DOI：10.1248/cpb.30.762

  日期：——

  The absolute configuration of P-1894B (vineomycin A1 (I)), a potent prolyl hydroxylase inhibitor, has been established as I from the absolute configuration of two sugar moieties (II, VI) obtained by chemical degradation of I.

  P-1894B （藤黄霉素 A1 (I)）是一种强效的脯氨酰羟化酶抑制剂，通过化学降解 I 得到的两个糖分子（II、VI）的绝对构型，确定其绝对构型为 I。
• Derivatives of Dihydroxypyrrolidine as Anti-Cancer Compounds
  申请人：EPFL Ecole Polytechnique Fédérale de Lausanne

  公开号：EP2067771A1

  公开（公告）日：2009-06-10

  The present invention relates to derivatives of dihydroxypyrrolidine useful in the treatment of cancer. The invention further relates to a process for making the compounds. The compounds are inhibitors of α mannosidase, and possibly, also inhibit nicotinamide phosphoribosyl transferase.

  本发明涉及一种二羟基吡咯烷衍生物，可用于癌症治疗。该发明还涉及一种制备该化合物的方法。该化合物是α甘露糖苷酶的抑制剂，可能也抑制烟酰胺磷酸核糖转移酶。
• A non-congener based synthesis of L-(-)-rhodinose and of a C4 hydroxyl protected derivative
  作者：Richard H. Schlessinger、Deborah D. Graves

  DOI：10.1016/s0040-4039(00)96515-8

  日期：1987.1

  A practical five step construction of the L-(-)-rhodinose derivative 1 and of L-(-)-rhodinose (2) from O-benzyl (S)-ethyl lactate is described. Optical rotations and other data for both 1 and 2 as well as for intermediates leading to them are provided.

  描述了由O-苄基（S）-乳酸生成的L-（-）-罗丹糖衍生物1和L-（-）-罗丹糖（2）的实际五步构建。提供了1和2以及导致它们的中间体的旋光度和其他数据。