((3S,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester | 87219-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((3S,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester
• 英文别名: (4-Methyl-5-oxo-tetrahydro-furan-3-YL)-carbamic acid benzyl ester；benzyl N-[(3S,4S)-4-methyl-5-oxooxolan-3-yl]carbamate
• CAS: 87219-31-6
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: NESTVCOYRAOPQU-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((3S,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 (3S,4S)-4-Amino-3-methyl-dihydro-furan-2-one; hydrobromide
  参考文献：
  名称：

  New Nodularins: A General Method for Structure Assignment

  摘要：

  A general method has been developed for assigning the structures of nodularin, a potent hepatotoxin, tumor promoter, and protein phosphatase inhibitor, and minor components isolated from a cultured and a bloom sample of the cyanobacterium Nodularia spumigena. It consists of (1) FABMS analysis (determination of molecular weight and molecular formula), (2) H-1 NMR spectroscopy on the parent compound and chiral GC analysis of an acid hydrolyzate (identification and stereochemistry of amino acid components), (3) ozonolysis followed by NaBH4 reduction (conversion to a linear peptide), and (4) FABMS/CID/MS analyses of the linear peptide and the parent compound (sequence analysis). The method has been employed in assigning structures to three new nodularins (2-4) and can be applied to other cyclic peptides containing alpha,beta-dehydroamino acid unit(s), especially the related microcystins, cyclic heptapeptide hepatotoxins. Two nodularins, [DMAdda(3)]nodularin (2) and [(6Z)-Adda(3)] nodularin (3), were obtained from a bloom sample collected from Lake Ellesmere (New Zealand), and [D-Asp(1)] nodularin (4) was isolated from cultured cells (strain L-575). The LD50s of 2 and 4 were 150 and 75 mu g/kg (ip, mice), respectively, but 3 did not show apparent toxicity at 2.0 mg/kg.

  DOI：

  10.1021/jo00088a014
• 作为产物：
  描述：

  (S)-Cbz-3-氨基-Y-丁内酯 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 ((3S,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester 、 (3R,4S)-3-methyl-4-N-(benzyloxycarbonylamino)butyrolactone
  参考文献：
  名称：

  New Nodularins: A General Method for Structure Assignment

  摘要：

  A general method has been developed for assigning the structures of nodularin, a potent hepatotoxin, tumor promoter, and protein phosphatase inhibitor, and minor components isolated from a cultured and a bloom sample of the cyanobacterium Nodularia spumigena. It consists of (1) FABMS analysis (determination of molecular weight and molecular formula), (2) H-1 NMR spectroscopy on the parent compound and chiral GC analysis of an acid hydrolyzate (identification and stereochemistry of amino acid components), (3) ozonolysis followed by NaBH4 reduction (conversion to a linear peptide), and (4) FABMS/CID/MS analyses of the linear peptide and the parent compound (sequence analysis). The method has been employed in assigning structures to three new nodularins (2-4) and can be applied to other cyclic peptides containing alpha,beta-dehydroamino acid unit(s), especially the related microcystins, cyclic heptapeptide hepatotoxins. Two nodularins, [DMAdda(3)]nodularin (2) and [(6Z)-Adda(3)] nodularin (3), were obtained from a bloom sample collected from Lake Ellesmere (New Zealand), and [D-Asp(1)] nodularin (4) was isolated from cultured cells (strain L-575). The LD50s of 2 and 4 were 150 and 75 mu g/kg (ip, mice), respectively, but 3 did not show apparent toxicity at 2.0 mg/kg.

  DOI：

  10.1021/jo00088a014

文献信息

• Development of chiral β-dicarbonyl equivalents. Enantiodivergent alkylation of aspartic acid.
  作者：Glenn J. McGarvey、Roger N. Hiner、Yoshio Matsubara、Taeboem Oh

  DOI：10.1016/s0040-4039(00)88008-9

  日期：1983.1
• New Nodularins: A General Method for Structure Assignment
  作者：Michio Namikoshi、Byoung Wook Choi、Ryuichi Sakai、Furong Sun、Kenneth L. Rinehart、Wayne W. Carmichael、William R. Evans、Phillip Cruz、Murray H. G. Munro、John W. Blunt

  DOI：10.1021/jo00088a014

  日期：1994.5

  A general method has been developed for assigning the structures of nodularin, a potent hepatotoxin, tumor promoter, and protein phosphatase inhibitor, and minor components isolated from a cultured and a bloom sample of the cyanobacterium Nodularia spumigena. It consists of (1) FABMS analysis (determination of molecular weight and molecular formula), (2) H-1 NMR spectroscopy on the parent compound and chiral GC analysis of an acid hydrolyzate (identification and stereochemistry of amino acid components), (3) ozonolysis followed by NaBH4 reduction (conversion to a linear peptide), and (4) FABMS/CID/MS analyses of the linear peptide and the parent compound (sequence analysis). The method has been employed in assigning structures to three new nodularins (2-4) and can be applied to other cyclic peptides containing alpha,beta-dehydroamino acid unit(s), especially the related microcystins, cyclic heptapeptide hepatotoxins. Two nodularins, [DMAdda(3)]nodularin (2) and [(6Z)-Adda(3)] nodularin (3), were obtained from a bloom sample collected from Lake Ellesmere (New Zealand), and [D-Asp(1)] nodularin (4) was isolated from cultured cells (strain L-575). The LD50s of 2 and 4 were 150 and 75 mu g/kg (ip, mice), respectively, but 3 did not show apparent toxicity at 2.0 mg/kg.