(1R,4R,4aR,5R,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,3,4,4a,5,7a-hexahydro-4-iodo-3-oxocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside | 318267-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (1R,4R,4aR,5R,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,3,4,4a,5,7a-hexahydro-4-iodo-3-oxocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside
• 英文别名: (4R)-3,4-dihydro-4-iodo-3-oxoperpivaloylaucubin；[(2R,3R,4S,5R,6S)-6-[[(1R,4R,4aR,5R,7aS)-5-(2,2-dimethylpropanoyloxy)-7-(2,2-dimethylpropanoyloxymethyl)-4-iodo-3-oxo-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 318267-54-8
• 化学式: C₄₅H₆₉IO₁₆
• 分子量: 992.938
• InChiKey: AISPBMSHCSXOCW-GCULPSKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (1R,4R,4aR,5R,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,3,4,4a,5,7a-hexahydro-4-iodo-3-oxocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (1R,3R,3aS,6R,6aR)-6-(2,2-dimethyl-1-oxopropoxy)-4-[(2,2-dimethyl-1-oxopropoxy)methyl]-3,3a,6,6a-tetrahydro-3-methoxy-1H-cyclopenta[1,2-c]furan-1-carboxylate 、 methyl (1R,3S,3aS,6R,6aR)-6-(2,2-dimethyl-1-oxopropoxy)-4-[(2,2-dimethyl-1-oxopropoxy)methyl]-3,3a,6,6a-tetrahydro-3-methoxy-1H-cyclopenta[1,2-c]furan-1-carboxylate 、 methyl (1S,3R,3aS,6R,6aR)-6-(2,2-dimethyl-1-oxopropoxy)-4-[(2,2-dimethyl-1-oxopropoxy)methyl]-3,3a,6,6a-tetrahydro-3-methoxy-1H-cyclopenta[1,2-c]furan-1-carboxylate 、 methyl (1S,3S,3aS,6R,6aR)-6-(2,2-dimethyl-1-oxopropoxy)-4-[(2,2-dimethyl-1-oxopropoxy)methyl]-3,3a,6,6a-tetrahydro-3-methoxy-1H-cyclopenta[1,2-c]furan-1-carboxylate
  参考文献：
  名称：

  摘要：

  Treatment of iodolactone 8a, having a cyclopentano[c]pyran skeleton and deriving from aucubin (1) (Scheme I), with sodium trimethylsilanolate permitted a straightforward rearrangement to bicyclo[3.1.0]hexenes 10a and 10b (Schemes 3 and 4). Introduction of an N-atom via a modified Curtius reaction provided an easy entry to fused aminocyclopentitols (Schemes 4 and 5). Target 4 is a conformationally restricted cyclopropane-fused analogue of the glycosidase inhibitors mannostatins A (2) and B (3).

  DOI：

  10.1002/1522-2675(20001004)83:10<2812::aid-hlca2812>3.0.co;2-7
• 作为产物：
  描述：

  perpivaloylaucubin 在 N-碘代丁二酰亚胺 、 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 (1R,4R,4aR,5R,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,3,4,4a,5,7a-hexahydro-4-iodo-3-oxocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  Treatment of iodolactone 8a, having a cyclopentano[c]pyran skeleton and deriving from aucubin (1) (Scheme I), with sodium trimethylsilanolate permitted a straightforward rearrangement to bicyclo[3.1.0]hexenes 10a and 10b (Schemes 3 and 4). Introduction of an N-atom via a modified Curtius reaction provided an easy entry to fused aminocyclopentitols (Schemes 4 and 5). Target 4 is a conformationally restricted cyclopropane-fused analogue of the glycosidase inhibitors mannostatins A (2) and B (3).

  DOI：

  10.1002/1522-2675(20001004)83:10<2812::aid-hlca2812>3.0.co;2-7

文献信息

• Stereoselective Conversion of Aucubin into Polyfunctionalized Tetrahydro-1H-cyclopenta[c]furan Glucosides
  作者：Christine Mouriès、Brigitte Deguin、Michel Koch、François Tillequin

  DOI：10.1002/hlca.200390005

  日期：2003.1

  azodicarboxylate gave (6R)-6-phthalimido-perpivaloylbartsioside (10) (Scheme 1). Selective oxidation reactions performed with perpivaloylaucubin (12) yielded (1R)- and (1S)-3(β-D-glucopyranosyloxy)-1H-cyclopenta[c]furan-1-carboxaldehydes 13 and 14 respectively (Scheme 2). Similarly, perpivaloyl-6-epiaucubin (9) and 10 afforded the corresponding (1S)-carboxaldehyde 15 and (1R)-carboxaldehyde 16, respectively. The

  2'，3'，4'，6'，10-penta- O-吡咯丙酸酯（6）与邻苯二甲酰亚胺，三苯基膦和偶氮二羧酸二乙酯的Mitsunobu反应得到（6 R）-6-邻苯二甲酰亚胺-过吡咯并戊二酮糖苷（10）（方案1））。用perpivaloylaucubin（12）进行的选择性氧化反应分别产生（1 R）-和（1 S）-3（β -D-吡喃葡萄糖基氧基）-1 H-环戊[ c ]呋喃-1-羧醛13和14（方案2） 。同样，perpivaloyl-6-epiaucubin（9）和10得到相应的（1S）-甲醛18和（1R）-甲醛16。以这种方式获得的受保护的环戊呋喃糖苷是通用的合成子，可能被证明可用于进一步的化学多样化。