methyl [O-β-D-glucopyranosyl-1,6]₂-D-glucopyranoside | 259669-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [O-β-D-glucopyranosyl-1,6]₂-D-glucopyranoside
• 英文别名: methyl 6-O-(6-O-β-D-glucopyranosyl)-β-D-glucopyranosyl-α-D-glucopyranoside；Glc(b1-6)Glc(b1-6)a-Glc1Me；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 259669-45-9
• 化学式: C₁₉H₃₄O₁₆
• 分子量: 518.469
• InChiKey: MOEWPYBRQOUAQN-FDIPLJRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  methyl 6-O-(6-O-(6-O-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-α-D-glucopyranoside 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以84.3%的产率得到methyl [O-β-D-glucopyranosyl-1,6]₂-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Applications of a Light-Fluorous Glycosyl Donor

  摘要：

  A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.

  DOI：

  10.1021/jo9000993

文献信息

• A fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker as a safety-catch linker
  作者：Hiroshi Tanaka、Yosuke Tanimoto、Tetsuya Kawai、Takashi Takahashi

  DOI：10.1016/j.tet.2011.09.030

  日期：2011.12

  We report on the fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker. The phenyl ether linker is stable under both acidic and basic conditions but can be cleaved under mildly acidic conditions after reduction to a vinyl ether. The utility of the method was demonstrated by the synthesis of a trisaccharide. A protected trisaccharide with a light-fluorous tag was directly prepared

  我们报告了使用苯基醚接头的低聚氟辅助合成。苯基醚接头在酸性和碱性条件下均稳定，但在还原为乙烯基醚后可在弱酸性条件下裂解。通过三糖的合成证明了该方法的实用性。通过使用三个结构单元通过一锅糖基化直接制备具有轻氟标签的被保护的三糖，所述三个结构单元包含通过苯醚具有轻氟标签的结构单元。三糖的桦木还原提供了完全脱保护的三糖，该三糖具有通过乙烯基醚连接的氟标签，该糖很容易通过固相萃取进行纯化。通过用3％TFA的MeOH溶液处理，将标签从糖部分上切下。
• IMMUNOMODULATING BETA-1,6-D-GLUCANS
  申请人：ImmuneXcite, Inc.

  公开号：US20170081428A1

  公开（公告）日：2017-03-23

  This invention relates to modifications of β-1,6-D-glucans, e.g., structures according to Formula (I), and the ability of these compositions to modulate an immune response.
• Synthesis and Applications of a Light-Fluorous Glycosyl Donor
  作者：Fa Zhang、Wei Zhang、Yan Zhang、Dennis P. Curran、Gang Liu

  DOI：10.1021/jo9000993

  日期：2009.3.20

  A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.