methyl 2,3-bis-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside | 182760-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-bis-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside
• 英文别名: 6-methoxy-7,8-bis(4-methoxy-benzyloxy)-2-(4-methoxyphenyl)hexahydropyrano[3,2-D]-[1,3]dioxine；(4aR,6S,7R,8S,8aR)-6-methoxy-2-(4-methoxyphenyl)-7,8-bis[(4-methoxyphenyl)methoxy]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 182760-09-4
• 化学式: C₃₁H₃₆O₉
• 分子量: 552.621
• InChiKey: XEIZGYYKSHKWSG-HMQNZOLESA-N

物化性质

• 沸点：
  665.8±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3-bis-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 在 三氯化铝 、 硼烷-三甲胺络合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以73%的产率得到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
• 作为产物：
  描述：

  tetrahydropyran-2-yl 2,3,4,6-tetra-O-acetyl-5-deoxy-5-thio-α-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.5h， 生成 methyl 2,3-bis-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxybenzylidene)-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

• NOVEL GLUCOPYRANOSE DERIVATIVES, PREPARATION THEREOF, AND BIOLOGICAL USES THEREOF
  申请人：Vachy Robert

  公开号：US20110136748A1

  公开（公告）日：2011-06-09

  The invention relates to a novel ester, the 3,5-di-tertiobutyl-4-hydroxybenzoate of 3,4,5-trihydroxy-6-methoxytetrahydropyran-2-yl methyl defined by the following formula (I). The invention also relates to the method for preparing the compound of formula (I) and to the use of said compound (I) to prepare a drug for treating and/or preventing enveloped virus infections.

  该发明涉及一种新型酯，即由以下公式（I）定义的3,5-二叔丁基-4-羟基苯甲酸3,4,5-三羟基-6-甲氧基四氢吡喃-2-基甲基。该发明还涉及制备公式（I）化合物的方法，以及利用该化合物（I）制备用于治疗和/或预防包膜病毒感染的药物。
• SN²Displacement of Carbohydrate Triflates by 9-Oximes of Erythromycin A and Of a Tylosin Derivative
  作者：Cyrille Grandjean、Gabor Lukacs

  DOI：10.1080/07328309608005695

  日期：1996.9

  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.
• Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units
  作者：Yasuharu Morii、Hiroko Matsuda、Keiichiro Ohara、Masaru Hashimoto、Kazuo Miyairi、Toshikatsu Okuno

  DOI：10.1016/j.bmc.2005.05.028

  日期：2005.9

  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.