(S)-[(2R,5S)-3,6-diethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol | 182368-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-[(2R,5S)-3,6-diethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 182368-88-3
• 化学式: C₁₈H₃₂N₂O₅
• 分子量: 356.462
• InChiKey: UUCTULPDTUVEAG-SEBNEYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-[(2R,5S)-3,6-diethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以95%的产率得到(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine
  参考文献：
  名称：

  基于氨基酸的非对映选择性合成elsaminose

  摘要：

  光学纯净的（+）-艾氨糖胺（2）是抗肿瘤抗生素艾素霉素A中所含的氨基糖，它是通过八步（总收率26％）从甘氨酸，L-缬氨酸和L-苏氨酸衍生而来的合成原料合成的。直接和关键中间体的选择性结构6，与完整的主链和适当的立体化学构型，是通过完成顺-aldol型反应锂化Schöllkopf的bislactime醚之间5和1,3-二氧戊环-4-甲醛（ - ） - 3。

  DOI：

  10.1016/0040-4039(96)01173-2
• 作为产物：
  描述：

  (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 、 (S)-2,5-二氢-3,6-二乙氧基-2-异丙基吡嗪 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以64%的产率得到(R)-[(2R,5S)-3,6-diethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol
  参考文献：
  名称：

  Amino acid based diastereoselective synthesis of fucosamines

  摘要：

  Enantiomerically pure (+)-D-fucosamine 1, (+)-N-methyl-D-fucosamine 2 and (+)-3-O-methyl-D-fucosamine 3 (elsaminose) have been synthesised from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 8 was accomplished by a highly syn,anti-selective aldol reaction between lithiated Schollkopf's bis-lactim ether 7 and the 1,3-dioxolane-4-carboxaldehyde 5. Elaboration of the common intermediate required optional methylation, selective hydrolysis of the bis-lactim ether in the presence of an isopropylidene ketal, lactonization and partial reduction of the carboxylic group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00376-2

文献信息

• Amino acid based diastereoselective synthesis of fucosamines
  作者：Marı́a Ruiz、Vicente Ojea、José M. Quintela

  DOI：10.1016/s0957-4166(02)00376-2

  日期：2002.8

  Enantiomerically pure (+)-D-fucosamine 1, (+)-N-methyl-D-fucosamine 2 and (+)-3-O-methyl-D-fucosamine 3 (elsaminose) have been synthesised from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 8 was accomplished by a highly syn,anti-selective aldol reaction between lithiated Schollkopf's bis-lactim ether 7 and the 1,3-dioxolane-4-carboxaldehyde 5. Elaboration of the common intermediate required optional methylation, selective hydrolysis of the bis-lactim ether in the presence of an isopropylidene ketal, lactonization and partial reduction of the carboxylic group. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Amino acid based diastereoselective synthesis of elsaminose
  作者：María Ruiz、Vicente Ojea、JoséMa Quintela

  DOI：10.1016/0040-4039(96)01173-2

  日期：1996.8

  Optically pure (+)-elsaminose (2), the amino sugar contained in the antitumour antibiotic elsamicin A, has been synthesized in eight steps (26% overall yield) from known building blocks derived from glycine, L-valine, and L-threonine. Direct and selective construction of the key intermediate 6, with the complete backbone and the proper stereochemical configuration, is accomplished by a syn-aldol type

  光学纯净的（+）-艾氨糖胺（2）是抗肿瘤抗生素艾素霉素A中所含的氨基糖，它是通过八步（总收率26％）从甘氨酸，L-缬氨酸和L-苏氨酸衍生而来的合成原料合成的。直接和关键中间体的选择性结构6，与完整的主链和适当的立体化学构型，是通过完成顺-aldol型反应锂化Schöllkopf的bislactime醚之间5和1,3-二氧戊环-4-甲醛（ - ） - 3。