Acetic acid 9-{(2S,3R,4S,5S,6R)-3,4-dihydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-(4-hydroxy-3-iodo-5,6-dimethoxy-2-methyl-benzoylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxyamino]-6-methyl-tetrahydro-pyran-2-yloxy}-naphtho[2,3-b]thiophen-4-yl ester | 108212-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid 9-{(2S,3R,4S,5S,6R)-3,4-dihydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-(4-hydroxy-3-iodo-5,6-dimethoxy-2-methyl-benzoylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxyamino]-6-methyl-tetrahydro-pyran-2-yloxy}-naphtho[2,3-b]thiophen-4-yl ester
• 英文别名: [9-[(2S,3R,4S,5S,6R)-3,4-dihydroxy-5-[[(2S,4S,5S,6R)-4-hydroxy-5-(4-hydroxy-5-iodo-2,3-dimethoxy-6-methylbenzoyl)sulfanyl-6-methyloxan-2-yl]oxyamino]-6-methyloxan-2-yl]oxybenzo[f][1]benzothiol-4-yl] acetate
• CAS: 108212-82-4
• 化学式: C₃₆H₄₀INO₁₃S₂
• 分子量: 885.749
• InChiKey: QCWCLIMBTVVCSQ-TUEBAGRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  245
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 Acetic acid 9-{(2S,3R,4S,5S,6R)-3,4-dihydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-(4-hydroxy-3-iodo-5,6-dimethoxy-2-methyl-benzoylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxyamino]-6-methyl-tetrahydro-pyran-2-yloxy}-naphtho[2,3-b]thiophen-4-yl ester
  参考文献：
  名称：

  Calichemicins, a novel family of antitumor antibiotics. 2. Chemistry and structure of calichemicin .gamma.1I

  摘要：

  DOI：

  10.1021/ja00245a051

文献信息

• Calicheamicins, a novel family of antitumor antibiotics. 4. Structure elucidation of calicheamicins .beta.1Br, .gamma.1Br, .alpha.2I, .alpha.3I, .beta.1I, .gamma.1I, and .delta.1I
  作者：May D. Lee、Theresa S. Dunne、Conway C. Chang、Marshall M. Siegel、George O. Morton、George A. Ellestad、William J. McGahren、Donald B. Borders

  DOI：10.1021/ja00029a030

  日期：1992.1

  The details of the structural assignment of the potent antitumor antibiotic, calicheamicin gamma-1I (6, C55H74IN3O21S4), is reported. Methanolysis studies on 6 and N-acetylcalicheamicin gamma-1I (8, C57H76IN3022S4) permitted the structural assignment of the glycosidic chain. Details of the spectral analysis supporting the assignments of the 3-O-methyl-alpha-L-rhamnopyranoside (D-ring) and the methyl 2,4-dideoxy-3-O-methyl-4-(N-acetyl-N-ethylamino)-a-L-xylopyranoside (E-ring) is reported. The structure of calicheamicinone (32, C18H17NO5S3), containing a bicyclo[7.3.1 ] tridec-9-ene-2,6-diyne system and a methyl trisulfide, was elucidated by a series of chemical degradation studies, which included an unexpected free radical cycloaromatization reaction. The presence of 4,6-dideoxy-4-(hydroxyamino)-beta-D-glucopyranoside (A-ring) and its N-O glycosidic linkage to the thio sugar (B-ring) was ascertained by X-ray crystallography of 24 (C36H40INO13S2), a degradation product of 6. The chemical structures of calicheamicins beta-1Br (1), gamma-1Br (2), alpha-2I (3), alpha-3I (4), beta-1I (5), and delta-1I (7) were assigned by correlating their H-1 and C-13 NMR data with that of calicheamicin gamma-1I. By tracking the biological activities of the degradation products, the enediyne system of calicheamicinone was shown to be essential for the DNA-damaging abilities of the calicheamicins. A mechanism whereby the enediyne could be triggered to cyclize via a 1,4-diyl, the putative DNA cleaving species, is proposed.