(S)-tert-Butoxycarbonylamino-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester | 172847-83-5

• 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: (S)-tert-Butoxycarbonylamino-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2S)-2-[(4S,5S)-5-(carbamoyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 172847-83-5
• 化学式: C₁₈H₂₇N₃O₁₀
• 分子量: 445.426
• InChiKey: AMZVZUMZOGLLKN-TVYUQYBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-tert-Butoxycarbonylamino-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 29.0h， 生成 多抗霉素
  参考文献：
  名称：

  Uchida, Kimio; Kato, Keisuke; Yamaguchi, Kentaro, Heterocycles, 2000, vol. 53, # 10, p. 2253 - 2259

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (S)-tert-Butoxycarbonylamino-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  A Convenient Synthesis of a N-Protected l-carbamoylpolyoxamic Acid Derivative: Total Synthesis of (+)-Polyoxin J and (+)-Polyoxin L

  摘要：

  DOI：

  10.1055/s-1999-3563

文献信息

• Total synthesis of (+)-polyoxin J
  作者：Alessandro Dondoni、Federico Junquera、Francisco L. Merchant、Pedro Merino、Tomas Tejero

  DOI：10.1039/c39950002127

  日期：——

  The antifungal antibiotic, polyoxin J 1, has been obtained (46.4%) by the coupling of a protected derivative of 5-O-carbamoylpolyoxamic acid 2 with thymine polyoxin C 3 which were prepared by a stereoselective aminohomologation strategy of sugar aldehydes (L-threose and dialdo-D-ribofuranose) employing nitrones 4 and 5 as their iminium derivatives and furan as a carboxylate group equivalent.

  抗真菌抗生素聚氧菌素J1（46.4%）是通过将5-O-氨基甲酰聚氧胺酸2的受保护衍生物与胸腺嘧啶聚氧菌素C3偶联得到的，后者是通过糖醛（L-苏糖和二醛-D-呋喃核糖）的立体选择性氨基同源化策略制备的，其中使用硝酮4和5作为亚氨基衍生物，呋喃作为羧酸基团等价物。
• Total Syntheses of (-)-Polyoxin J and (-)-Polyoxin L
  作者：Hiroyuki Akita、Kimio Uchida、Keisuke Kato

  DOI：10.3987/com-97-s(n)59

  日期：——

  A convenient synthesis of the N-protected L-carbamoyl-polyoxamic acid derivative (7) from 4-O-tert-butyldiphenylsilyl-2,3-isopropylidene-L-threose (8) using vinylmagnesium bromide and its application to the total syntheses of the peptidyl nucleoside antibiotics, polyoxins J (1) and L (2), are described.
• Applications of Sugar Nitrones in Synthesis:  The Total Synthesis of (+)-Polyoxin J¹
  作者：Alessandro Dondoni、Santiago Franco、Federico Junquera、Francisco L. Merchán、Pedro Merino、Tomás Tejero

  DOI：10.1021/jo9702913

  日期：1997.8.1

  A convergent synthesis of the peptidyl nucleoside antibiotic (inhibitor of chitin biosynthesis) polyoxin J (2) by coupling of 5-O-carbamoyl polyoxamic acid (3) and thymine polyoxin C (4) is described. These compounds were prepared by chain elongation and amination of sugar-derived aldehydes employing their nitrones as iminium derivatives and the furan ring as a masked carboxyl. Thus, the stereoselective addition of 2-lithiofuran to the L-threose derived N-benzyl nitrone 5 followed by reduction of the resulting hydroxylamine to amine, carbamoylation of the free hydroxy group, and oxidative cleavage of the furan ring to the carboxylate group gave a protected derivative of 3 (30%). The same method was followed for the synthesis of the ribofuranosyl alpha-amino acid nucleoside 4 (12.6%) starting from the D-ribose derived nitrone 6. The final coupling was performed by the N-hydroxysuccinimide active ester method in DMSO with the Hunig base (i-Pr2EtNH) using a derivative of 3 and unprotected 4.