methyl 6-O-(5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside | 146558-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: 5-thio-Glc(a1-6)a-Glc1Me；(2S,3R,4S,5S,6R)-2-methoxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)thian-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 146558-13-6
• 化学式: C₁₃H₂₄O₁₀S
• 分子量: 372.394
• InChiKey: CBQWWUJAQQIOAZ-JQAKRLNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6-O-(5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside 在 吡啶 作用下， 生成 methyl 6-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,3,4-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Hashimoto, Hironobu; Kawanishi, Masashi; Yuasa, Hideya, Chemistry - A European Journal, 1996, vol. 2, # 5, p. 556 - 560

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose 在 4 A molecular sieve 、 氨 、 三乙基硅基三氟甲磺酸酯 、 sodium 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl 6-O-(5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides

  摘要：

  The synthesis of methyl and allyl 5'-thio-alpha-D-kojibiosides and methyl 5'-thio-alpha-D-isomaltoside is described. The phenylselenoglycoside and trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-5-thioglucose have been employed as glycosyl donors to glycosylate glucopyranosyl accepters with 2-OH and 6-OH positions free. The disaccharides thus obtained are potential glucosidase inhibitors. The conformational preferences of allyl 5'-thiokojibioside (34) were studied by comparison of experimental NOE curves with the theoretical counterparts for the corresponding methyl glycoside 25, derived from a Boltzmann-averaged grid search using the program PIMM91. Very goad agreement of experimental NOE curves derived from selective NOE measurements with the theoretical curves is found. The data are consistent with the population of a global minimum structure Phi=-43, Psi-39 degrees) to the extent of 90%, and a second local minimum (Phi=-36, Psi=-173 degrees) to the extent of 6%. An X-ray crystal structure of 34 at 190 K (R=4.2%) indicates a conformation (Phi=-46, Psi=-23 degrees) that is similar to that of the global minimum.

  DOI：

  10.1016/s0957-4166(00)80386-9

文献信息

• Unprecedented chemical glycosidation of 5-thioglucose to give disaccharides.
  作者：Seema Mehta、B.Mario Pinto

  DOI：10.1016/0040-4039(93)88013-9

  日期：1992.12

  3,4,6-tetra-O-acetyl-5-thioglucopyranose when used to glycosylate selectively protected glucopyranosyl acceptors with the 2-OH and 6-OH positions free affords the 1,2-linked and the 1,6-linked disaccharides as a 3:1 and 1.5:1 α:β mixture, respectively.

  2,3,4,6-四-O-乙酰基-5-硫代吡喃葡萄糖的糖基三氯乙酰亚氨酸酯，用于糖基化带有2-OH和6-OH位置的选择性保护的吡喃葡萄糖基受体时，会提供1,2-连接的和1 ，6-连接的二糖分别为3：1和1.5：1α：β混合物。
• 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.
• α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units
  作者：Hiroko Matsuda、Keiichiro Ohara、Yasuharu Morii、Masaru Hashimoto、Kazuo Miyairi、Toshikatsu Okuno

  DOI：10.1016/s0960-894x(03)00072-6

  日期：2003.3

  A general method for alpha-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue. (C) 2003 Elsevier Science Ltd. All rights reserved.