1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dimethoxybenzylamino)-β-D-glucopyranose | 405290-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dimethoxybenzylamino)-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[(2,4-dimethoxyphenyl)methylamino]oxan-2-yl]methyl acetate
• CAS: 405290-27-9
• 化学式: C₂₃H₃₁NO₁₁
• 分子量: 497.499
• InChiKey: FIHRPYOGBXFRHZ-GNJRFXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  145
• 氢给体数：
  1
• 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-(2,4-dimethoxybenzylamino)-β-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 3-nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glycopyranoside
  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 、 水 为溶剂， 反应 1.0h， 以5.91 g的产率得到1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dimethoxybenzylamino)-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