N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,2-diethoxycarbonyl-4-phenyl-4-oxothiobutanamide | 213838-31-4

• 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: N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,2-diethoxycarbonyl-4-phenyl-4-oxothiobutanamide
• 英文别名: diethyl 2-phenacyl-2-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]carbamothioyl]propanedioate
• CAS: 213838-31-4
• 化学式: C₃₀H₃₇NO₁₄S
• 分子量: 667.688
• InChiKey: XEOSQHXULLGTQJ-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  228
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,2-diethoxycarbonyl-4-phenyl-4-oxothiobutanamide 在 磷酸 、 乙酸酐 作用下， 反应 12.0h， 以76%的产率得到diethyl 5-phenyl-2-sulfanylidene-1-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]pyrrole-3,3-dicarboxylate
  参考文献：
  名称：

  Reactions of per-O-acetylglucosyl isothiocyanate with carbon bases. A new method for the stereocontrolled syntheses of nucleosides and glucosylaminothiophenes

  摘要：

  Reaction of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylisothiocyanate 5 with diethyl malonate in a basic medium gave the corresponding glucopyranosyl thioamide without significant deacetylation. This thioamide in solution presents Z-anti as the sole configuration. Reactions of 5 with carbanions which have an ethoxycarbonyl group are a way to prepare anomerically pure N-nucleoside derivatives of pyrrole and tetrahydropyridine. Reactions of 5 with carbanions stabilized by one cyano group are used to prepare glucosylamino thiophenes with only the B-configuration. Some other stereochemical aspects of the prepared compounds are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00243-2
• 作为产物：
  描述：

  丙二酸二乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 反应 0.67h， 生成 N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,2-diethoxycarbonyl-4-phenyl-4-oxothiobutanamide
  参考文献：
  名称：

  Reactions of per-O-acetylglucosyl isothiocyanate with carbon bases. A new method for the stereocontrolled syntheses of nucleosides and glucosylaminothiophenes

  摘要：

  Reaction of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylisothiocyanate 5 with diethyl malonate in a basic medium gave the corresponding glucopyranosyl thioamide without significant deacetylation. This thioamide in solution presents Z-anti as the sole configuration. Reactions of 5 with carbanions which have an ethoxycarbonyl group are a way to prepare anomerically pure N-nucleoside derivatives of pyrrole and tetrahydropyridine. Reactions of 5 with carbanions stabilized by one cyano group are used to prepare glucosylamino thiophenes with only the B-configuration. Some other stereochemical aspects of the prepared compounds are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00243-2