methyl D-arabinopyranoside | 884655-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl D-arabinopyranoside
• 英文别名: Methylarabinosid；METHYL-beta-D-ARABINO-PYRANOSIDE；(3S,4R,5R)-2-methoxyoxane-3,4,5-triol
• CAS: 884655-09-8
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: ZBDGHWFPLXXWRD-VRPWFDPXSA-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 D-arabinopyranoside 在 硫酸 、 sodium hydride 、 溶剂黄146 、 二甲基亚砜 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (2R,3S,4R)-2,3,4-tri-benzyloxy-6-phenylhex-5-en-1-ol
  参考文献：
  名称：

  使用氯磺酰基异氰酸酯对聚苄基醚进行区域选择性和非对映选择性胺化：1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇和（-）-龙胆碱的总合成。

  摘要：

  通过使用CSI的区域选择性和非对映选择性NHCbz导入，化学选择性去除Cbz保护和闭环易位作为关键步骤，由D-lyxose精确地完成了DAB1（1）和（-）-lentiginosine（2）的总合成。

  DOI：

  10.1021/ol061614x
• 作为产物：
  描述：

  甲醇 、 D-arabinofuranose 在 盐酸 作用下， 反应 24.0h， 生成 methyl D-arabinopyranoside
  参考文献：
  名称：

  吡喃糖的立体选择性C-糖基化反应：甘露糖基阳离子的构象偏好和反应

  摘要：

  进行了与甘露糖和其他吡喃糖酶有关的缩醛的C-糖基化的系统研究。C-5烷氧基烷基仅对立体选择性提供适度的影响。另一方面，对在C-2，C-3和C-4处带有烷氧基的戊基吡喃糖的研究表明，烷氧基对选择性有重要影响。甘露糖的情况下，与观察到的高选择性α Ç -mannosylation反向以高选择性β如果C-5的烷氧基烷基中除去。对中间氧碳鎓离子（包括甘露糖基阳离子）的构象偏爱的分析，以及对亲核进攻过渡态中产生的空间效应的考虑，为这些现象提供了解释。

  DOI：

  10.1021/jo0522963

文献信息

• Efficient isomerization of methyl arabinofuranosides into corresponding arabinopyranosides in presence of pyridine
  作者：Sunchu Prabhakar、Loïc Lemiègre、Thierry Benvegnu、Srinivas Hotha、Vincent Ferrières、Laurent Legentil

  DOI：10.1016/j.carres.2016.07.014

  日期：2016.10

  Fisher glycosylation, the oldest but efficient reaction towards alkyl glycosides, suffers nonetheless from lack of selectivity, especially when dealing with pentoses. In this case, a mixture of the four isomers, namely the furanosides and the pyranosides, is formed. According to previous studies, the rate and selectivity of the reaction depend greatly on the reaction time and the temperature. In this

  Fisher糖基化是对烷基糖苷的最古老但有效的反应，但仍缺乏选择性，特别是在处理戊糖时。在这种情况下，形成了呋喃糖苷和吡喃糖苷这四种异构体的混合物。根据先前的研究，反应的速率和选择性很大程度上取决于反应时间和温度。在本报告中，评估了另一个因素，即弱亲核碱基的引入。有趣的是，在反应开始几小时后添加吡啶使得甲基戊呋喃糖苷快速异构化为其吡喃糖苷对应物。使用阿拉伯糖，核糖，木糖和lyxose作为起始戊糖，反应以极高的非对映选择性进行。
• Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates
  作者：Kajitha Suthagar、Matthew I. J. Polson、Antony J. Fairbanks

  DOI：10.1039/c5ob00851d

  日期：——

  Arabino N-glycosyl sulfamides, sulfonamides and sulfamates convert from the furanose to the thermodynamically preferred pyranose form in aqueous solution.

  阿拉伯糖基磺酰胺、磺酰胺和磺酸酯在水溶液中从呋喃糖转化为热力学上更为稳定的吡喃糖形式。
• Bashir, Nazir B.; Phythian, Sara J.; Reason, Andrew J., Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2203 - 2222
  作者：Bashir, Nazir B.、Phythian, Sara J.、Reason, Andrew J.、Roberts, Stanley M.

  DOI：——

  日期：——
• Direct Glycosylation of Unprotected and Unactivated Sugars Using Bismuth Nitrate Pentahydrate
  作者：Innaiah K. Polanki、Siva H. Kurma、Asish K. Bhattacharya

  DOI：10.1080/07328303.2015.1028585

  日期：2015.5.4

  Bi(NO3)(3), a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high alpha-selectivity. Further, an expedient separation of alpha- and beta-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.
• Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity
  作者：Aditya K. Sanki、Julie Boucau、Parijat Srivastava、Samuel S. Adams、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1016/j.bmc.2008.03.062

  日期：2008.5

  The emergence of drug resistant tuberculosis necessitates a search for new antimycobacterial compounds. The antigen 85 (ag85) complex is a family of mycolyl transferases involved in the synthesis of trehalose-6,6'-dimycolate and the mycolated hexasaccharide motif found at the terminus of the arabinogalactan in mycobacterium. Enzymes involved in the synthesis of cell wall structures like these are potential targets for the development of new antiinfectives. To potentially inhibit the ag85 complex, methyl 5-S-alkyl-5-thio-arabinofuranoside analogues were designed based on docking studies with ag85C derived from Mycobacterium tuberculosis. The target arabinofuranosides were then synthesized and the antibacterial activity evaluated against Mycobacterium smegmatis ATCC 14468. Two of the compounds, 5-S-octyl-5-thio-alpha-D-arabinofuranoside (8) and 5-S-octyl-5-thio-beta-D-arabinofuranoside (11), showed MICs of 256 and 512 mu g/mL, respectively. Attempts to directly evaluate acyltransferase inhibitory activity of the arabinofuranosides against ag85C are also described. In conclusion, a new class of antimycobacterial arabinofuranosides has been discovered. Published by Elsevier Ltd.