methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside | 18944-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: Methyl-α-4-benzoyl-olivosid；[(2R,3S,4R,6S)-4-hydroxy-6-methoxy-2-methyloxan-3-yl] benzoate
• CAS: 18944-96-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: GBBTYIBCVJGZKH-FOUMNBMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 在 platinum(IV) oxide sodium azide 、 ammonium chloride 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 35.5h， 生成 methyl α-D-acosaminide
  参考文献：
  名称：

  甲基3-氨基-2,3,6-三苯氧基-α-D-阿拉伯糖基己吡喃糖苷和手性中间体的合成噻吩霉素的替代制备。

  摘要：

  DOI：

  10.1016/0008-6215(84)85014-4
• 作为产物：
  描述：

  [(2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3,4-dihydro-2H-pyran-3-yl] benzoate 在 偶氮二异丁腈 、 polystyrene-bound silyl triflate 、 三正丁基氢锡 、 氟化氢吡啶 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 71.03h， 生成 methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  The First Polymer-Assisted Solution-Phase Synthesis of Deoxyglycosides

  摘要：

  [GRAPHICS]A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(1) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.

  DOI：

  10.1021/ol016545v

文献信息

• Efficient Synthesis of the Deoxysugar Part of Versipelostatin by Direct and Stereoselective Glycosylation and Revision of the Structure of the Trisaccharide Unit
  作者：Hiroshi Tanaka、Atsushi Yoshizawa、Shuhei Chijiwa、Jun-ya Ueda、Motoki Takagi、Kazuo Shin-ya、Takashi Takahashi

  DOI：10.1002/asia.200800448

  日期：2009.7.6

  Sweets for my sweet! Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosidation of the reduced VST aglycon. Comparison of the synthetic and natural VST products using NMR indicate that VST has a β‐d‐digitoxose‐(1,4)‐α‐l‐oleandrose‐(1,4)‐β‐d‐digitoxose trisaccharide. A biological assay indicates that the deoxyoligosaccharide unit of the

  糖果给我带来甜蜜！通过减少的VST糖苷配基的直接和立体选择性糖苷化，可实现VersipeloSTatin（VST）的脱氧糖部分的有效合成。使用NMR对合成和天然VST产品进行的比较表明，VST具有一个β-d-地氧糖-（1,4）-α-l-oleandrose-（1,4）-β-d-地氧糖三糖。生物学测定表明，合成糖苷的脱氧寡糖单元对于生物学活性很重要。
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Direct and Stereoselective Synthesis of β-Linked 2,6-Deoxyoligosaccharides
  作者：Hiroshi Tanaka、Atsushi Yoshizawa、Takashi Takahashi

  DOI：10.1002/anie.200604031

  日期：2007.3.26
• Synthesis of 2,3,6-Trideoxysugar-Containing Disaccharides by Cyclization and Glycosidation through the Sequential Activation of Sulfoxide and Methylsulfanyl Groups in a One-Pot Procedure
  作者：Toru Amaya、Daisuke Takahashi、Hiroshi Tanaka、Takashi Takahashi

  DOI：10.1002/anie.200250218

  日期：2003.4.25
• Negative-Ion Mass Spectrometry of Carbohydrates. A Mechanistic Study of the Fragmentation Reactions of Dideoxy Sugars
  作者：Roger W. Binkley、Edith R. Binkley、Shaoming Duan、Michael J. S. Tevesz、Witold Winnik

  DOI：10.1080/07328309608005697

  日期：1996.9

  Hydroxyl group deprotonation of the alpha and beta anomers of methyl 3-O-benzyl-2,6-dideoxy-D-arabino-hexopyranoside (1 and 2) occurs readily in the gas phase to produce the corresponding anions 3 and 4, respectively. Collisionally activated dissociation (CAD) of these anions causes fragmentation reactions that include ring opening, E2 elimination, and decarbonylation. Mechanisms for these reactions are proposed, and these mechanisms are supported by study of partially deuterated analogs of 1 and 2.