methyl 2,3,4-tri-O-benzoyl-6-O-[2',3',4',6'-[tetrakis-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-α-D-glucopyranoside | 565462-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-O-[2',3',4',6'-[tetrakis-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-α-D-glucopyranoside
• 英文别名: Mob(-2)[Mob(-3)][Mob(-4)][Mob(-6)]5-thio-Glc(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-2-[[(2S,3R,4S,5S,6R)-3,4,5-tris[(4-methoxyphenyl)methoxy]-6-[(4-methoxyphenyl)methoxymethyl]thian-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 565462-84-2
• 化学式: C₆₆H₆₈O₁₇S
• 分子量: 1165.32
• InChiKey: AJYRQOYWUOFUGV-UAWMWFRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  84
• 可旋转键数：
  30
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  206
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-[2',3',4',6'-[tetrakis-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-α-D-glucopyranoside 在 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 methyl 6-O-(5'-thio-α-D-glucopyranosyl)-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 5-deoxy-5-thio-α-D-glucopyranoside 在 盐酸 、 三乙基硅基三氟甲磺酸酯 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 methyl 2,3,4-tri-O-benzoyl-6-O-[2',3',4',6'-[tetrakis-O-(4-methoxyphenyl)methyl]-5'-deoxy-5'-thio-α-D-glucopyranosyl]-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

• 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.