[(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate | 87678-03-3

• 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: [(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 87678-03-3
• 化学式: C₁₈H₂₆O₇S
• 分子量: 386.466
• InChiKey: IYIQYSAUDMPPFI-PMPSAXMXSA-N

物化性质

• 沸点：
  481.9±40.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate 在 四丁基溴化铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 7-Chloro-1-((2S,3R,4R)-2,3,4,5-tetrahydroxy-pentyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
  参考文献：
  名称：

  Synthesis and amphiphilic properties of glycosyl-1,4-benzodiazepin-2,5-diones

  摘要：

  Glycosyl-l,4-benzodiazepin-2,5-diones were prepared by coupling polyhydroxylated groups at N-1 of the corresponding benzodiazepine. The groups include 1-deoxy-D,L-xylit-1-yl, 6-deoxy-D-glucopyranos-6-yl, and 6-deoxy-3-O-R-D-glucopyranos-6-yl (R = n-CnH2n+1 n = 8, 12, and 16). The structural variations of the sugar group allowed comparison of such amphiphilic data as water solubility (Sw), critical micelle concentration (CMC), and corresponding surface tension (gamma) values. At 25 degrees C, unsubstituted benzodiazepines have Sw values from 0.9 to 4.2 10(-3) mol L-1, whereas xylit-1-yl and 6-deoxy-D-glucopyranos-6-yl derivatives are, respectively, 7.4-25 and 58-204 times more soluble. Also, compounds with R = n-C8H17 are more soluble than corresponding benzodiazepines (1.4-5.8 times) and give micelles with CMC from 2.7 to 5.6 10-3 mol L-1 and corresponding gamma from 29 to 37 mN m(-1). In contrast, compounds with R = n-C12H25 and n-C16H33 are not soluble enough to reach the critical micelle concentration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00163-4
• 作为产物：
  描述：

  diacetonexylitol 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 [(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  First Total Synthesis of Panaxytriol, a Potent Antitumor Agent Isolated from Panax Ginseng

  摘要：

  首次合成了从三七中分离出来的一种强效抗肿瘤药物--三七三醇 1，并确认其立体结构为 (3R,9R,10R)-十七碳-1-烯-4,6-二炔-3,9,10-三醇。

  DOI：

  10.1055/s-1998-1775

文献信息

• SHONO, TATSUYA;MATSUMURA, YOSHIHIRO;HAMAGUCHI, HIROSHI;NAITOH, SHIGEKI, J. ORG. CHEM., 1983, 48, N 25, 5126-5128
  作者：SHONO, TATSUYA、MATSUMURA, YOSHIHIRO、HAMAGUCHI, HIROSHI、NAITOH, SHIGEKI

  DOI：——

  日期：——