methyl 2,3-di-O-tert-butyldimethylsilyl-β-D-galactofuranoside | 1351685-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-tert-butyldimethylsilyl-β-D-galactofuranoside
• 英文别名: (1R)-1-[(2S,3S,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxyoxolan-2-yl]ethane-1,2-diol
• CAS: 1351685-99-8
• 化学式: C₁₉H₄₂O₆Si₂
• 分子量: 422.71
• InChiKey: ROYMKBNPFGNBKJ-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-tert-butyldimethylsilyl-β-D-galactofuranoside 在 吡啶 、 咪唑 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 methyl 5,6-anhydro-2,3-di-O-tert-butyldimethylsilyl-α-L-altrofuranoside
  参考文献：
  名称：

  Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase

  摘要：

  合成、分子建模及抑制性质的描述，这些性质是模拟病原微生物糖蛋白质中的β-d-Galf-(1 → 5)-d-Galf基序的呋喃糖硫代二糖。

  DOI：

  10.1039/c5ra06899a
• 作为产物：
  描述：

  methyl (methyl β-D-galactofuranosid)uronate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 29.0h， 生成 methyl 2,3-di-O-tert-butyldimethylsilyl-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase

  摘要：

  合成、分子建模及抑制性质的描述，这些性质是模拟病原微生物糖蛋白质中的β-d-Galf-(1 → 5)-d-Galf基序的呋喃糖硫代二糖。

  DOI：

  10.1039/c5ra06899a

文献信息

• Synthesis of Branched Dithiotrisaccharides via Ring-Opening Reaction of Sugar Thiiranes
  作者：Evangelina Repetto、Verónica E. Manzano、María Laura Uhrig、Oscar Varela

  DOI：10.1021/jo2018685

  日期：2012.1.6

  (3→3)-disulfide 19, which resulted from the oxidative dimerization of 17. However, the S-acetyl derivative of 17 could be obtained in good yield (62%) by LiAlH4 reduction of the crude mixture 17–19, followed by acetylation. The same sequence of reactions starting from 14 and the 1-thiolate of Galp afforded the per-O,S-acetyl derivative of Galp-β-S-(1→4)-3,4-dithio-α-d-Glcp-O-iPr (23), which was selectively

  描述了从各自的六呋喃糖或六吡喃糖环氧前体合成5，6-和3，4-噻喃衍生物的令人满意的程序。通过1-thioaldoses硫杂丙环的受控开环反应物成功地完成，得到选择性，区域选择性和立体选择性，β-小号- （1→4）-3,4- dithiodisaccharides。例如，过-O-乙酰基-1-硫代葡萄糖（16）对2-丙基2,6-二-O-乙酰基-3,4-表硫基-α- d-吡喃半乳糖苷的C-4的区域选择性攻击（14）），得到衍生物GLC的p -β-小号- （1→4）-3,4- dithioGlc p - ø -我PR（17）。该硫二糖伴有在16和17之间形成的（1→3）-二硫化物18和对称的（3→3）-二硫化物19，这是由于17的氧化二聚作用而引起的。然而，小号-乙酰基衍生物的17可以以良好的收率（62％）的LiAlH通过获得4还原粗混合物的17 - 19，接着乙酰化。从开始反应的相同序列14和Gal的1
• Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase
  作者：Evangelina Repetto、Carla Marino、Oscar Varela

  DOI：10.1016/j.bmc.2013.02.057

  日期：2013.6

  A new (1 -> 6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl alpha,beta-D-galactofuranosid) uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-beta-D-galactofuranoside (2 beta) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-beta-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target beta-D-Galf-S-(1 -> 6)-beta-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the beta-galactofuranosidase from Penicillum fellutanum (K-i = 3.62 mM). (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-<scp>d</scp>-galactofuranosidase
  作者：Marcos J. Lo Fiego、Carla Marino、Oscar Varela

  DOI：10.1039/c5ra06899a

  日期：——

  Description of the synthesis, molecular modeling and inhibitory properties of furanosyl thiodisaccharides that are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf, found in glycoconjugates of pathogenic microorganisms.

  合成、分子建模及抑制性质的描述，这些性质是模拟病原微生物糖蛋白质中的β-d-Galf-(1 → 5)-d-Galf基序的呋喃糖硫代二糖。