methyl 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-5-deoxy-α-D-allohexofuranuronate 1,2,3-triacetate | 858662-10-9

• 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: methyl 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-5-deoxy-α-D-allohexofuranuronate 1,2,3-triacetate
• 英文别名: methyl (2S)-2-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-2-[(2R,3R,4R,5R)-3,4,5-triacetyloxyoxolan-2-yl]acetate
• CAS: 858662-10-9
• 化学式: C₂₅H₃₃NO₁₁
• 分子量: 523.537
• InChiKey: JXUUGGBURWSOJD-IIDPUWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  37
• 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：
  144
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-5-deoxy-α-D-allohexofuranuronate 1,2,3-triacetate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.01h， 生成 methyl 5-N-benzylamino-5-deoxy-α-D-allohexofuranuronate 1,2,3-triacetate hydrochloride
  参考文献：
  名称：

  A formal synthesis of thymine polyoxin C

  摘要：

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.034
• 作为产物：
  描述：

  5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-5-deoxy-D-glycero-D-alloheptofuranose 1,2,3-triacetate 在 lead(IV) acetate 、 溴 、 碳酸氢钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.17h， 生成 methyl 5-[N-benzyl-N-[(1,1-dimethylethoxy)carbonyl]amino]-5-deoxy-α-D-allohexofuranuronate 1,2,3-triacetate
  参考文献：
  名称：

  A formal synthesis of thymine polyoxin C

  摘要：

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.034