methyl α,β-L-glucopyranoside | 753481-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α,β-L-glucopyranoside
• 英文别名: methyl L-glucoside；Methyl-α-L-glucopyranose；methyl L-glucopyranoside；(2S,3R,4R,5S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 753481-53-7
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: HOVAGTYPODGVJG-VOJFLOGESA-N

物化性质

• 沸点：
  389.1±42.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α,β-L-glucopyranoside 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  杯红霉素 A：不对称总合成和结构测定

  摘要：

  我们报告了杯红霉素 A 的第一个不对称全合成和结构测定。利用模块化策略，开发了一种简洁的方法来组装具有内酯 A 环的两种对映异构体的六环骨架。立体选择性糖基化将有角的六环框架与单糖片段偶联以产生杯红霉素 A 及其立体异构体。这使我们能够确定和分配 C-25 (25S) 和单糖（l-葡萄糖的衍生物）的绝对构型。

  DOI：

  10.1021/acs.orglett.1c00193
• 作为产物：
  描述：

  甲醇 、 L-(-)-glucose 在 乙酰氯 作用下， 生成 methyl α,β-L-glucopyranoside
  参考文献：
  名称：

  杯红霉素 A：不对称总合成和结构测定

  摘要：

  我们报告了杯红霉素 A 的第一个不对称全合成和结构测定。利用模块化策略，开发了一种简洁的方法来组装具有内酯 A 环的两种对映异构体的六环骨架。立体选择性糖基化将有角的六环框架与单糖片段偶联以产生杯红霉素 A 及其立体异构体。这使我们能够确定和分配 C-25 (25S) 和单糖（l-葡萄糖的衍生物）的绝对构型。

  DOI：

  10.1021/acs.orglett.1c00193

文献信息

• L-Sucrose and process for producing same
  申请人：Queen's University at Kingston

  公开号：US04207413A1

  公开（公告）日：1980-06-10

  L-sucrose or .beta.-L-fructofuranosyl .alpha.-L-glucopyranoside--(I), the enantiomer of naturally occuring D-sucrose, which does not appear in nature has been synthesized and has been found to be sweet. It is unlikely that L-sucrose is metabolized in the manner of D-sucrose. In a preferred process for producing L-sucrose the key step is the condensation of 2,3,4,6-tetra-O-benzyl-.alpha.-L-glucopyranosyl chloride--(II) with 1,3,4,6-tetra-O-benzyl-L-fructofuranose--(III). Compound II is obtained from L-glucose by way of 2,3,4,6-tetra-O-benzyl-.alpha.-L-glucopyranose; and L-glucose is prepared from L-arabinose by nitromethane synthesis. Compound III is obtained by oxidation, with Jones reagent, of 1,3,4,6-tetra-O-benzyl-L-mannitol which, in turn, is prepared from L-mannose. The condensation product of II and III is catalytically debenzylated to produce L-sucrose.

  L-蔗糖或β-L-果糖呋喃基-α-L-葡萄糖苷（I），是天然存在的D-蔗糖的对映体，不会出现在自然界中，已被合成，并被发现具有甜味。 L-蔗糖不太可能像D-蔗糖那样被代谢。 在制备L-蔗糖的首选工艺中，关键步骤是将2,3,4,6-四-O-苯甲酰-α-L-葡萄糖苷氯化物（II）与1,3,4,6-四-O-苯甲酰-L-果糖呋喃糖（III）缩合。化合物II是通过2,3,4,6-四-O-苯甲酰-α-L-葡萄糖苷制备的，而L-葡萄糖则通过硝基甲烷合成法从L-阿拉伯糖制备而来。化合物III是通过Jones试剂氧化1,3,4,6-四-O-苯甲酰-L-甘露醇获得的，而1,3,4,6-四-O-苯甲酰-L-甘露醇则是由L-甘露糖制备而来。 II和III的缩合产物通过催化脱苯甲基可产生L-蔗糖。
• Caminoside A, an Antimicrobial Glycolipid Isolated from the Marine Sponge <i>Caminus sphaeroconia</i>
  作者：Roger G. Linington、Marilyn Robertson、Annick Gauthier、B. Brett Finlay、Rob van Soest、Raymond J. Andersen

  DOI：10.1021/ol0268337

  日期：2002.11.1

  [GRAPHICS]Extracts of the marine sponge Caminus sphaeroconia showed potent activity in a screen for bacterial type III secretion inhibitors. Bioassay guided fractionation of the extract led to the isolation of the novel antimicrobial glycollpid caminoside A (1). The structure of caminoside A was elucidated by analysis of spectroscopic data and chemical degradation.
• Antimycobacterial 1,4-napthoquinone natural products from Moneses uniflora
  作者：Haoxin Li、Allyson Bos、Stéphanie Jean、Duncan Webster、Gilles A. Robichaud、John A. Johnson、Christopher A. Gray

  DOI：10.1016/j.phytol.2018.07.032

  日期：2018.10

  new 1,4-naphthoquinone derivative, 5,8-dihydro-3-hydroxychimaphilin (4) and five known compounds (1, 2 and 5-7) were isolated from an extract of the Canadian medicinal plant Moneses uniflora that significantly inhibited the growth of Mycobacterium tuberculosis H37Ra. The structure of 4 was established through analysis of NMR and MS data and the absolute configuration of the glycone of 5 was determined by chemical transformation and comparison with standards prepared from D- and L-glucose. All compounds isolated were screened against Mycobacterium tuberculosis (H37Ra) and the mammalian HEK 293 cell line and, with the exception of compounds 5 and 7, exhibited marked selectivity in their bioactivity: Compound 1 exhibited potent antimycobacterial activity (IC50 of 5.4 mu M) and moderate cytotoxicity (IC50 of 30 mu M); compounds 2, 4 and 6 showed moderate antimycobacterial activity (IC50 values from 28 to 47 mu M) without affecting the viability of mammalian cells; compound 5 displayed moderate activity in both assays (IC50 values of 44 and 55 mu M respectively); and compound 7 was not active in either assay. These data suggest that the Moneses napthaquinone derivatives elicit biological responses in mycobacterial and mammalian cells through disparate modes of action that warrant further investigation.
• US4207413A
  申请人：——

  公开号：US4207413A

  公开（公告）日：1980-06-10
• US9180111B2
  申请人：——

  公开号：US9180111B2

  公开（公告）日：2015-11-10