2-deoxy-3,4-di-O-acetyl-α-L-rhamnopyranose | 127112-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-3,4-di-O-acetyl-α-L-rhamnopyranose
• 英文别名: [(2S,3S,4S,6R)-3-acetyloxy-6-hydroxy-2-methyloxan-4-yl] acetate
• CAS: 127112-87-2
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: AUHYUSJXUNPACJ-RAWIJENESA-N

物化性质

• 沸点：
  314.1±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-deoxy-3,4-di-O-acetyl-α-L-rhamnopyranose 在 Grubbs catalyst first generation polymer-bound PPh₃*HBr 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 28.0h， 生成 1,4-di-(3',4'-di-O-acetyl-2',6'-dideoxy-α-L-arabino-hexopyranosidly)-2-butene
  参考文献：
  名称：

  Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties

  摘要：

  The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C-2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.013
• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 三苯基膦氢溴酸盐 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以33.333%的产率得到
  参考文献：
  名称：

  稀有糖的 氟导向的1,2-反式糖基化†

  摘要：

  为了调和迫切需要访问定义明确的β-构型的2,6-二-脱氧吡喃糖类似物以进行化学生物学处理，以及天然系统固有的α-选择性，已经研究了氟在C2上的直接作用。局部部分电荷反转（C-H δ + →C-F δ - ）引起的基于基底的α-立体选择性的反转，而不管保护基电子设备。

  DOI：

  10.1039/c6ob00025h

文献信息

• Organoboron-Catalyzed Regio- and Stereoselective Formation of β-2-Deoxyglycosidic Linkages
  作者：Thomas M. Beale、Patrick J. Moon、Mark S. Taylor

  DOI：10.1021/ol501711v

  日期：2014.7.3

  A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.
• Synthesis of 2-deoxy sugars from glycals
  作者：Subramaniam Sabesan、Susana Neira

  DOI：10.1021/jo00018a054

  日期：1991.8