1,3,4,6-tetra-O-acetyl-2-deoxy-2-(N-(2,4-dimethoxybenzyl)-acetamido)-β-D-glucopyranose | 405290-28-0

• 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: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(N-(2,4-dimethoxybenzyl)-acetamido)-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-5-[acetyl-[(2,4-dimethoxyphenyl)methyl]amino]-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 405290-28-0
• 化学式: C₂₅H₃₃NO₁₂
• 分子量: 539.537
• InChiKey: JVGGZSVQMRDMTA-FXEFVXDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(N-(2,4-dimethoxybenzyl)-acetamido)-β-D-glucopyranose 在 molecular sieve 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-(N-(2,4-dimethoxybenzyl)-acetamido)-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  2,4-DIMETHOXYBENZYL: AN AMIDE PROTECTING GROUP FOR 2-ACETAMIDO GLYCOSYL DONORS1

  摘要：

  2,4-Dimethoxybenzyl (Dmob) was used as an amide protecting group for 2-acetamido glycosyl donors. The N-Dmob group was introduced by imine formation between 2,4-dimethoxybenzaldehyde and d-glucosamine, followed by per-O-acylation, reduction to form the amine, and finally N-acetylation to give 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dimetboxybenzylacetamido)-beta -D-glucopyranose. Selective 1-O-deacetylation and treatment with trichloroacetonitrile gave the corresponding trichloroacetimidate glycosyl donor. Lewis acid-promoted glycosylations of the model substrate 3-nitrobenzyl alcohol gave exclusively the P-glycoside product, either with or without the Dmob protecting group remaining depending on the reagent and conditions employed. The N-Dmob protected 1-O-acetate glucosyl donor gave higher glycosylation yields than the corresponding 2-acetamido glucosyl donor without Dmob protection.

  DOI：

  10.1081/car-100108272
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dimethoxybenzylideneamino)-β-D-glucopyranose 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(N-(2,4-dimethoxybenzyl)-acetamido)-β-D-glucopyranose
  参考文献：
  名称：

  2,4-DIMETHOXYBENZYL: AN AMIDE PROTECTING GROUP FOR 2-ACETAMIDO GLYCOSYL DONORS1

  摘要：

  2,4-Dimethoxybenzyl (Dmob) was used as an amide protecting group for 2-acetamido glycosyl donors. The N-Dmob group was introduced by imine formation between 2,4-dimethoxybenzaldehyde and d-glucosamine, followed by per-O-acylation, reduction to form the amine, and finally N-acetylation to give 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dimetboxybenzylacetamido)-beta -D-glucopyranose. Selective 1-O-deacetylation and treatment with trichloroacetonitrile gave the corresponding trichloroacetimidate glycosyl donor. Lewis acid-promoted glycosylations of the model substrate 3-nitrobenzyl alcohol gave exclusively the P-glycoside product, either with or without the Dmob protecting group remaining depending on the reagent and conditions employed. The N-Dmob protected 1-O-acetate glucosyl donor gave higher glycosylation yields than the corresponding 2-acetamido glucosyl donor without Dmob protection.

  DOI：

  10.1081/car-100108272