[(2R,3R,4R,6S)-6-[(2S,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate | 199486-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,6S)-6-[(2S,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
• CAS: 199486-49-2
• 化学式: C₇₀H₉₇Cl₂NO₃₈
• 分子量: 1631.43
• InChiKey: UPADRKHAIMTUCC-XJHHDZPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  111
• 可旋转键数：
  22
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  482
• 氢给体数：
  8
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,6S)-6-[(2S,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 29.0h， 以50%的产率得到
  参考文献：
  名称：

  EVERNINOMICIN抗生素C16正构异构体的绝对立体化学测定; 丙烯酸的新型酸催化异构化

  摘要：

  通过新型的酸催化原酸酯异构化，明确地建立了Ziracin（1）的C16原酸酯中心的绝对立体化学。通过化学降解和广泛的光谱分析来确定所得异构体2和3的结构。这种新的异构化成功地扩展到了其他相关的everninomicins（11-13），从而完成了everninomicin抗生素的整个结构分配。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)10178-2
• 作为产物：
  描述：

  依维米星 在 对硝基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 [(2R,3R,4R,6S)-6-[(2S,2'R,3'S,3aS,4S,4'R,6R,7R,7aS)-4-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',6,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate 、 [(2R,3R,4R,6S)-6-[(2S,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
  参考文献：
  名称：

  EVERNINOMICIN抗生素C16正构异构体的绝对立体化学测定; 丙烯酸的新型酸催化异构化

  摘要：

  通过新型的酸催化原酸酯异构化，明确地建立了Ziracin（1）的C16原酸酯中心的绝对立体化学。通过化学降解和广泛的光谱分析来确定所得异构体2和3的结构。这种新的异构化成功地扩展到了其他相关的everninomicins（11-13），从而完成了everninomicin抗生素的整个结构分配。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)10178-2

文献信息

• Ganguly, Journal of the Indian Chemical Society, 1997, vol. 74, # 11-12, p. 980 - 986
  作者：Ganguly

  DOI：——

  日期：——
• DETERMINATION OF THE ABSOLUTE STEREOCHEMISTRY AT THE C16 ORTHOESTER OF EVERNINOMICIN ANTIBIOTICS; A NOVEL ACID-CATALYZED ISOMERIZATION OF ORTHOESTERS
  作者：Ashit K Ganguly、Jinping L McCormick、Tze-Ming Chan、Anil K Saksena、Pradip R Das

  DOI：10.1016/s0040-4039(97)10178-2

  日期：1997.11

  The absolute stereochemistry at C16 orthoester center of Ziracin (1) was unequivocally established via a novel acid-catalyzed orthoester isomerization. Structures of the resulting isomers 2 and 3 were determined by chemical degradation and extensive spectroscopic analyses. This novel isomerization was successfully extended to other related everninomicins (11–13), thus completing the entire structural

  通过新型的酸催化原酸酯异构化，明确地建立了Ziracin（1）的C16原酸酯中心的绝对立体化学。通过化学降解和广泛的光谱分析来确定所得异构体2和3的结构。这种新的异构化成功地扩展到了其他相关的everninomicins（11-13），从而完成了everninomicin抗生素的整个结构分配。©1997爱思唯尔科学有限公司。