methyl β-D-arabinofuranoside | 22861-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-D-arabinofuranoside
• 英文别名: methyl β-D-lyxofuranoside；beta-d-Lyxofuranoside, methyl；(2R,3R,4S,5R)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
• CAS: 22861-09-2
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: NALRCAPFICWVAQ-DPYQTVNSSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  348.7±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)：
  -1.93
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl β-D-arabinofuranoside 、 乙酸酐 在 吡啶 作用下， 生成 Acetic acid (2R,3S,4S,5R)-4-acetoxy-2-acetoxymethyl-5-methoxy-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Dahlhoff, Wilhelm V., Liebigs Annalen der Chemie, 1990, # 11, p. 1093 - 1096

  摘要：

  DOI：
• 作为产物：
  描述：

  [(3aS,4R,6R,6aS)-2-ethyl-4-methoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaborol-6-yl]methyl acetate 、 甲醇 生成 methyl β-D-arabinofuranoside
  参考文献：
  名称：

  DAHLHOFF, WILHELM V., LIEBIGS ANN. CHEM.,(1990) N1, C. 1093-1096

  摘要：

  DOI：

文献信息

• HPLC Analysis of the Product Distribution in the Iodine-Catalyzed Methyl Glycosidation of Pentoses and 6-Deoxyhexoses
  作者：Gyöngyi Gyémánt、András Lipták

  DOI：10.1080/07328309808002897

  日期：1998.4

  The product distribution of the iodine-catalyzed methyl glycosidation of four pentoses (D-ribose, D-arabinose, D-xylose, and D-lyxose) and two 6-deoxyhexoses (L-rhamnose, and D-fucose) was studied by HPLC using an APS column (dihydrogen sulphate form) with different acetonitrile-water mobile phases. In agreement with earlier results, a temperature dependent on-column isomerization was observed for all the investigated aldoses, except for ribose. The first-eluted furanosides were followed by pyranosides, and the free sugars were eluted last with the highest retention volumes.
• Gold(III)-Catalyzed Glycosidations for 1,2-<i>trans</i> and 1,2-<i>cis</i> Furanosides
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/jo501052y

  日期：2014.8.15

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.
• A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines
  作者：Emma M. Dangerfield、Shivali A. Gulab、Catherine H. Plunkett、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.carres.2010.03.016

  日期：2010.7

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.
• JAROSZ, SLAWOMIR, BULL. POL. ACAD. SCI. CHEM., 36,(1988) N-8, C. 327-332
  作者：JAROSZ, SLAWOMIR

  DOI：——

  日期：——
• DAHLHOFF, WILHELM V., LIEBIGS ANN. CHEM.,(1990) N1, C. 1093-1096
  作者：DAHLHOFF, WILHELM V.

  DOI：——

  日期：——