(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 | 182216-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 182216-93-9
• 化学式: C₁₈H₃₂N₂O₅
• 分子量: 356.462
• InChiKey: UUCTULPDTUVEAG-KHMAMNHCSA-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：

  (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 在 盐酸 、 四丁基碘化铵 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 53.0h， 生成 ethyl (2R,3R,4S,5R)-3-benzyloxy-4,5-isopropylidenedioxy-2-[N-methyl-M-(diphenylmethyl)amino]hexanoate
  参考文献：
  名称：

  Asymmetric Synthesis of D-Fucosamine and N-Methyl-D-Fucosamine

  摘要：

  (+)-D-岩藻糖胺和(+)-N-甲基-D-岩藻糖胺（新卡西诺司他汀的氨基糖分子）是由天然氨基酸衍生的已知结构单元合成的。通过 Schöllkopf 的双内酰胺醚 2 和 1,3-二氧戊环-4-甲醛 3 之间的合成-醛类反应，直接非对映选择性地合成了关键中间体 4。由普通氨基酯 7 衍生出的奥唐纳席夫碱通过还原和单甲基化反应可获得 N-甲基衍生物。

  DOI：

  10.1055/s-1997-696
• 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

• Asymmetric Synthesis of D-Fucosamine and <i>N</i>-Methyl-D-Fucosamine
  作者：Vicente Ojea、María Ruiz、José Quintela

  DOI：10.1055/s-1997-696

  日期：——

  (+)-D-fucosamine and (+)-N-methyl-D-fucosamine (the amino sugar moiety of neocarzinostatin) have been synthesized from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 4 was accomplished by a syn-aldol type reaction between Schöllkopf's bislactim ether 2 and the 1,3-dioxolane-4-carboxaldehyde 3. Reduction and monomethylation of a O'Donnell's Schiff base derived from the common amino ester 7 allows an optional access to the N-methyl derivative.

  (+)-D-岩藻糖胺和(+)-N-甲基-D-岩藻糖胺（新卡西诺司他汀的氨基糖分子）是由天然氨基酸衍生的已知结构单元合成的。通过 Schöllkopf 的双内酰胺醚 2 和 1,3-二氧戊环-4-甲醛 3 之间的合成-醛类反应，直接非对映选择性地合成了关键中间体 4。由普通氨基酯 7 衍生出的奥唐纳席夫碱通过还原和单甲基化反应可获得 N-甲基衍生物。
• 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。
• 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.