methyl 2,3,6-tri-O-(4-methoxyphenyl)methyl-α-D-glucopyranoside | 182760-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-(4-methoxyphenyl)methyl-α-D-glucopyranoside
• CAS: 182760-10-7
• 化学式: C₃₁H₃₈O₉
• 分子量: 554.637
• InChiKey: SXJOBUQXCPMDSD-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.07
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-(4-methoxyphenyl)methyl-α-D-glucopyranoside 在 吡啶 、 18-冠醚-6 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 Erythromycin A (E)-9-{O-[methyl 2,3,6-tri-O-(4-methoxybenzyl)-α-D-galactopyranosid-4-yl]oxime}
  参考文献：
  名称：

  SN²Displacement of Carbohydrate Triflates by 9-Oximes of Erythromycin A and Of a Tylosin Derivative

  摘要：

  The preparation of 9-O-glycosyloxime derivatives of erythromycin A (1) and tylosin (2) is reported. Access to this new class of macrolides was achieved from (E)-9-oxime of erythromycin A (3) and 9-oxime of tylosin 20-(1,3-dithiane) (4), by successful displacement of triflates of suitably protected carbohydrates.

  DOI：

  10.1080/07328309608005695
• 作为产物：
  描述：

  tetrahydropyran-2-yl 4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside 在 三氯化铝 、 硼烷-三甲胺络合物 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.5h， 生成 methyl 2,3,6-tri-O-(4-methoxyphenyl)methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

  摘要：

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.028

文献信息

• Ligand‐Controlled Stereoselective Synthesis and Biological Activity of 2‐Exomethylene Pseudo‐glycoconjugates: Discovery of Mincle‐Selective Ligands
  作者：Takahiro Ikazaki、Eri Ishikawa、Hiroto Tamashima、Hisako Akiyama、Yusuke Kimuro、Makoto Yoritate、Hiroaki Matoba、Akihiro Imamura、Hideharu Ishida、Sho Yamasaki、Go Hirai

  DOI：10.1002/anie.202302569

  日期：2023.5.22

  Phosphine-ligand-controlled Tsuji–Trost-type glycosylation enabled the stereoselective synthesis of α- and β-pseudo-glycoconjugates with an exomethylene group at the C2 position. These compounds are Mincle-selective ligands that do not bind to CD1d, suggesting that the 2-OH group of natural glycoconjugates is critical for CD1d binding.

  膦配体控制的 Tsuji-Trost 型糖基化使得能够立体选择性合成在 C2 位置具有外亚甲基基团的 α- 和 β- 假糖缀合物。这些化合物是不与 CD1d 结合的 Mincle 选择性配体，表明天然糖缀合物的 2-OH 基团对 CD1d 结合至关重要。