methyl L-lyxopyranoside | 2500-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl L-lyxopyranoside
• 英文别名: (3R,4R,5S)-2-methoxyoxane-3,4,5-triol
• CAS: 2500-78-9
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: ZBDGHWFPLXXWRD-JMSAOHGTSA-N

物化性质

• 沸点：
  314.0±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

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：

  methyl L-lyxopyranoside 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 TEA 、 氢气 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4-Phospholanetriol, 5-[(acetyloxy)methyl]-1-ethyl-, triacetate,1-oxide
  参考文献：
  名称：

  Nakamura, Y.; Yamamoto, H.; Inokawa, S., Heterocycles, 1984, vol. 21, # 2, p. 505

  摘要：

  DOI：
• 作为产物：
  描述：

  D-galacturonic acid 在 盐酸 、 sodium tetrahydroborate 、 iron(III) sulfate 、 双氧水 、 calcium carbonate 作用下， 生成 methyl L-lyxopyranoside
  参考文献：
  名称：

  Nakamura, Y.; Yamamoto, H.; Inokawa, S., Heterocycles, 1984, vol. 21, # 2, p. 505

  摘要：

  DOI：

文献信息

• Stereospecific Synthesis of Glycoside Mimics Through Migita‐Kosugi‐Stille Cross‐Coupling Reactions of Chemically and Configurationally Stable 1‐ <i>C</i> ‐Tributylstannyl Iminosugars
  作者：Sizhe Li、Justyna Jaszczyk、Xavier Pannecoucke、Thomas Poisson、Olivier R. Martin、Cyril Nicolas

  DOI：10.1002/adsc.202000886

  日期：2021.1.19

  A process for the de novo synthesis of imino‐C‐glycosides is described. The methodology is based on the reaction of 1‐C‐stannylated iminosugars with various electrophiles under the conditions of Migita‐Kosugi‐Stille cross‐couplings, which gives 1‐C‐substituted iminosugar derivatives in a stereoretentive process. The required iminoglycosyl stannanes are obtained by way of the highly stereoselective

  一种用于处理所述从头合成的亚氨基Ç -glycosides进行说明。该方法基于在Migita-Kosugi-Stille交叉偶联条件下1C锡烷基化的亚氨基糖与各种亲电试剂的反应，从而在立体保持过程中生成1 C取代的亚氨基糖衍生物。所需iminoglycosyl锡烷由高立体选择性加成tributylstannyllithium至（的方式获得小号ř或（ - ）小号小号） - ñ -叔-butanesulfinyl葡基胺，接着是激活环化序列。最有趣的是，该方法是可调的：锡加合物的构型仅由叔丁烷亚磺酰基助剂，因此在成环后即可获得“α”构型或“β”构型的亚氨基糖基锡烷。在随后的立体保持性CC键形成过程中，该方法允许以受控方式合成亚氨基C糖基化合物的假异构体。
• Stereoselective synthesis of 1,1′-linked α-l-lyxopyranosyl β-d-glucopyranoside, the proposed biosynthetic precursor of the FG ring system of avilamycins
  作者：Magnus S. Schmidt、Valentin Wittmann

  DOI：10.1016/j.carres.2008.05.004

  日期：2008.7

  The non-reducing disaccharide beta-d-Glcp-(1<-->1)-alpha-L-Lyxp1 had been proposed to be an early intermediate during the biosynthesis of avilamycin A [Boll, R.; Hofmann, C.; Heitmann, B.; Hauser, G.; Glaser, S.; Koslowski, T.; Friedrich, T.; Bechthold, A. J. Biol. Chem.2006, 281, 14756-14763]. This work describes a comparison of two strategies for the synthesis of 1 and its 2-amino-2-deoxy analog

  已经提出非还原性二糖β-d-Glcp-（1→1）-α-L-Lyxp1是阿维霉素A生物合成过程中的早期中间体[Boll，R。； J.Biol.Chem。，1992，5，5]。霍夫曼角；Heitmann，B .；Hauser，G .；Glaser，S .; T. Koslowski；弗里德里希（T.）Bechthold，AJ Biol。化学，2006，281，14756-14763]。这项工作描述了两种合成1及其2-氨基-2-脱氧类似物的策略，其中葡萄糖或溶糖部分作为糖基供体。用2,3,4-三-O-乙酰基-α-L-lypypyyranosyl三氯乙酰亚胺酸酯13可获得最佳的立体选择性和收率。13与2,3,4,6-四-O-乙酰基-的反应D-吡喃葡萄糖以1∶1，1′α和1β，1′β异构体的混合物形式以10∶1的比例产生二糖，产率为50％。13和3,4的反应 6-三-O-乙酰基-2-叠氮基-2-脱氧
• Design, Synthesis, and Antiviral Activity of α-Nucleosides:  <scp>d</scp>- and <scp>l</scp>-Isomers of Lyxofuranosyl- and (5-Deoxylyxofuranosyl)benzimidazoles
  作者：Michael T. Migawa、Jean-Luc Girardet、John A. Walker、George W. Koszalka、Stanley D. Chamberlain、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm970545c

  日期：1998.4.1

  Several 2-substituted alpha-D- and alpha-L-lyxofuranosyl and 5-deoxylyxofuranosyl derivatives of 5,6-dichloro-2-(isopropylamino)-1- -(beta-L-ribofuranosyl)benzimidazole (1263W94) and 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were synthesized and evaluated for activity against two herpesviruses (HSV-1 and HCMV) and for their cytotoxicity against HFF and KB cells. Condensation of 1,2,3,5-tetra-O-acetyl-L-lyxofuranose (2a) with 2,5,6-trichlorobenzimidazole (1) yielded the or-nucleoside 3a. The 2-bromo derivative and 2-methylamino derivative were prepared by treatment of 3a with HBr followed by deprotection or from methylamine, respectively. Compound 3a was deprotected and the resultant nucleoside used to prepare the 2-cyclopropylamino and 2-isopropylamino derivatives. The 2-alkylthio nucleosides were prepared by condensing 2a with 5,6-dichlorobenzimidazole-2-thione followed by deprotection. Alkylation of this adduct gave the 2-methylthio and 2-benzylthio derivatives. Condensation of 5-deoxy-1,2,3-tri-O-acetyl-L-lyxofuranosyl, prepared from L-lyxose, with 1 or 2-bromo-5,6-dichlorobenzimidazole (15), followed by deprotection, gave the 2-chloro or 2-bromo-5'-deoxylyxofuranosyl derivative, respectively. The cyclopropylamino derivative was prepared from the 2-chloro derivative. All D-isomers were prepared in an analogous fashion from D-lyxose. Either compounds were inactive against HSV-1 or weak activity was poorly separated from cytoxicity. In contrast, the 2-halogen derivatives in both the alpha-lyxose and 5-deoxy-alpha-lyxose series were active against the Towne strain of HCMV. The 5-deoxy alpha-L analogues were the most active, IC50's = 0.2-0.4 mu M, plaque assay; IC90's = 0.2-2 mu M, yield reduction assay. All of the 2-isopropylamino or 2-cyclopropylamino derivatives were less active (IC50's = 60-100 mu M, plaque assay; IC90's = 17-100 mu M, yield reduction assay) and were not cytotoxic. The methylamino, thio, and methylthio derivatives were neither active nor cytotoxic. The benzylthio derivatives were weakly active, but this activity was poorly separated from cytotoxicity. The alpha-lyxose L-isomers were more active in a plaque assay against the AD169 strain of HCMV compared to the Towne strain, thereby providing additional evidence of antiviral specificity.