4-nitrophenyl 6-O-(5'-deoxy-5'-thio-β-D-glucopyranosyl)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 6-O-(5'-deoxy-5'-thio-β-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: p-nitrophenyl 5'-thio-α-gentiobioside；5-thio-Glc(b1-6)Glc(a)-O-Ph(4-NO2)；(2R,3R,4S,5S,6R)-2-(4-nitrophenoxy)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)thian-2-yl]oxymethyl]oxane-3,4,5-triol
• 化学式: C₁₈H₂₅NO₁₂S
• 分子量: 479.462
• InChiKey: WUNUFEMLWIIDCM-GSPJEIBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  240
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  对硝基苯-α-D-葡萄糖吡喃苷 在 吡啶 、 甲酸 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-nitrophenyl 6-O-(5'-deoxy-5'-thio-β-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

• β-Selective Glycosylation of 5-Thioglucopyranose Derivatives; Syntheses of β-(1→6) Linked 5′-Thioglucopyranosyl Disaccharides
  作者：Keiichiro Ohara、Hiroko Matsuda、Masaru Hashimoto、Kazuo Miyairi、Toshikatsu Okuno

  DOI：10.1246/cl.2002.626

  日期：2002.6

  was achieved by performing the reaction with pivaloyl- or benzoyl-protected glucopyranosyl trichloroacetimidates and BF3OEt2, a glycosyl activator, when C6-OH glucopyranosyl or galactopyranosyl derivatives were employed as acceptors.

  当使用 C6-OH 吡喃葡萄糖基或吡喃半乳糖衍生物作为受体时，通过与新戊酰基或苯甲酰基保护的吡喃葡萄糖基三氯乙酰亚胺酯和 BF3OEt2（一种糖基活化剂）进行反应，实现了与 5-硫代吡喃葡萄糖的 β-立体选择性和有效糖基化。
• 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.