O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-trichloroacetimidate | 146558-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-trichloroacetimidate
• 英文别名: 2,3,4,6-tetra-O-acetyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxythian-2-yl]methyl acetate
• CAS: 146558-06-7
• 化学式: C₁₆H₂₀Cl₃NO₉S
• 分子量: 508.761
• InChiKey: LOYUYVHBZXPUBI-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-trichloroacetimidate 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  合成4-氰基苯基1,5-二硫代-β-D-吡喃葡萄糖苷及其6-脱氧以及6-脱氧-5-烯衍生物作为口服抗血栓药。

  摘要：

  在三氟甲磺酸三甲基甲硅烷基酯的存在下，将5-硫代-D-吡喃葡萄糖五乙酸酯与4-氰基苯硫醇缩合，得到4-氰基苯基2,3,4,6-四-O-乙酰基-1,5-二硫代-α-D-吡喃葡萄糖苷7和3,4,6-三-O-乙酰基-2,5-脱水5-硫代-D-甘露糖双（4-氰基苯基）二硫缩醛9的比例为2：3。后者可能由4-氰基苯基2,3,4,6-四-O-乙酰基-1,5-二硫基-β-D-吡喃葡萄糖苷6通过环硫原子的跨环参与而形成。当使用2,3,4,6-四-O-乙酰基-5-硫代α-D-吡喃葡萄糖基溴作为供体，并且反应在碳酸钾存在下进行时，则6，7，4，4-氰基- 2-（2,3,4,6-四-O-乙酰基-5-硫代-α-D-吡喃葡萄糖基）苯基和4-氰基-2-（2,3,4,6-四-O-乙酰基-以23：4：2：1的比例形成5-硫代-β-D-吡喃葡萄糖基）苯基1,5-二硫代-β-D-吡喃葡萄糖苷（14和16）。讨论了14和16的形成机理。在碳酸钾存在下，将2

  DOI：

  10.1016/s0008-6215(97)10041-6
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 在 乙酸肼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-trichloroacetimidate
  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

• 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。
• 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。
• Anti-hypercholesterolemic compounds
  申请人：Sings L. Heather

  公开号：US20070135357A1

  公开（公告）日：2007-06-14

  The instant invention provides novel cholesterol absorption inhibitors of Formula I and the pharmaceutically acceptable salts and esters thereof. The compounds are useful for lowering plasma cholesterol levels, particularly LDL cholesterol, and for treating and preventing atherosclerosis and atherosclerotic disease events.

  本发明提供了一种新型的胆固醇吸收抑制剂，其化学式为I，并且其药学上可接受的盐和酯。这些化合物可用于降低血浆胆固醇水平，特别是LDL胆固醇，并用于治疗和预防动脉粥样硬化和动脉粥样硬化疾病事件。
• 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.
• Mehta; Andrews; Johnston, Journal of the American Chemical Society, 1994, vol. 116, # 4, p. 1569 - 1570
  作者：Mehta、Andrews、Johnston、Pinto

  DOI：——

  日期：——