tert-butyl N-[(2R)-1-[[(3R,3'S,4'R)-1,4'-dimethyl-2,2'-dioxospiro[indole-3,5'-oxolane]-3'-yl]amino]-3-methylsulfanyl-1-oxopropan-2-yl]carbamate | 1356133-09-9

• 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: tert-butyl N-[(2R)-1-[[(3R,3'S,4'R)-1,4'-dimethyl-2,2'-dioxospiro[indole-3,5'-oxolane]-3'-yl]amino]-3-methylsulfanyl-1-oxopropan-2-yl]carbamate
• CAS: 1356133-09-9
• 化学式: C₂₂H₂₉N₃O₆S
• 分子量: 463.555
• InChiKey: GZJYCQJGOAGVKP-YJCWTPFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R)-1-[[(3R,3'S,4'R)-1,4'-dimethyl-2,2'-dioxospiro[indole-3,5'-oxolane]-3'-yl]amino]-3-methylsulfanyl-1-oxopropan-2-yl]carbamate 在 sodium periodate 、 silica gel 作用下， 以 甲醇 、 对二甲苯 、 水 为溶剂， 反应 24.67h， 生成 maremycin B S-oxide
  参考文献：
  名称：

  Total synthesis of maremycins A, B, C1/C2, D1, and D2

  摘要：

  The total synthesis of maremycins A, B, C-1/C-2, D-1, and D-2 is achieved starting from the natural amino acids L-isoleucine and S-methyl-L-cysteine, in which the total synthesis of maremycins B, C-1/C-2, and D-2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-beta-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.118
• 作为产物：
  描述：

  (2S,3S)-methyl 3-methyl-2-(2,2,2-trifluoroacetamido)pentanoate 在 吡啶 、 咪唑 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 草酰氯 、 acetyl hypobromite 、 pyridine hydrofluoride 、 氧气 、 silver nitrate 、 溶剂黄146 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 、 锌 、 苯酚 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 303.5h， 生成 tert-butyl N-[(2R)-1-[[(3R,3'S,4'R)-1,4'-dimethyl-2,2'-dioxospiro[indole-3,5'-oxolane]-3'-yl]amino]-3-methylsulfanyl-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Total synthesis of maremycins A, B, C1/C2, D1, and D2

  摘要：

  The total synthesis of maremycins A, B, C-1/C-2, D-1, and D-2 is achieved starting from the natural amino acids L-isoleucine and S-methyl-L-cysteine, in which the total synthesis of maremycins B, C-1/C-2, and D-2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-beta-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.118

文献信息

• Total synthesis of maremycins A, B, C1/C2, D1, and D2
  作者：Yonghua Liu、Liangren Zhang、Yanxing Jia

  DOI：10.1016/j.tetlet.2011.11.118

  日期：2012.2

  The total synthesis of maremycins A, B, C-1/C-2, D-1, and D-2 is achieved starting from the natural amino acids L-isoleucine and S-methyl-L-cysteine, in which the total synthesis of maremycins B, C-1/C-2, and D-2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-beta-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. (C) 2011 Elsevier Ltd. All rights reserved.