(3S)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-pentenoic acid tert-butyl ester | 1235201-09-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-pentenoic acid tert-butyl ester
• CAS: 1235201-09-8
• 化学式: C₂₃H₃₄O₁₂
• 分子量: 502.516
• InChiKey: AHKDMCFMHITEOC-KCHUAEFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-pentenoic acid tert-butyl ester 在 甲醇 、 sodium hydride 作用下， 反应 1.5h， 以100%的产率得到(3S)-3-(β-D-glucopyranosyloxy)-4-pentenoic acid tertbutyl ester
  参考文献：
  名称：

  Efficient synthesis of the functional central core lactides, a constituent of antibiotic fattiviracins

  摘要：

  An efficient convergent synthetic method has been developed for preparation of various stereoisomers and derivatives of fattiviracins via a common lactide. The synthetic route comprises seco acids prepared by the beta-selective glycosylation of chiral 3-hydroxy-4-pentanoate obtained by enzymatic kinetic resolution. The regioselective protection of four individual hydroxy groups was achieved via the 4,6-O-benzylidenation of the glucose moiety from its TMS ethers. The dimeric cyclization of the seco acids under control of reaction concentration afforded the desired lactide without using KH. Our convergent synthetic method was successfully applied to direct installation of side chains to the lactide by cross metathesis to synthesize fattiviracin derivatives. We achieved improvements to the reported method with respect to: (1) synthesis of a convergent synthetic intermediate; (2) stereoselectivity in glycosylation; and (3) establishment of a low cost route suitable for large scale synthesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.007
• 作为产物：
  描述：

  2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 、 (3S)-3-羟基-4-戊烯酸叔丁酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以77%的产率得到(3S)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-pentenoic acid tert-butyl ester
  参考文献：
  名称：

  Efficient synthesis of the functional central core lactides, a constituent of antibiotic fattiviracins

  摘要：

  An efficient convergent synthetic method has been developed for preparation of various stereoisomers and derivatives of fattiviracins via a common lactide. The synthetic route comprises seco acids prepared by the beta-selective glycosylation of chiral 3-hydroxy-4-pentanoate obtained by enzymatic kinetic resolution. The regioselective protection of four individual hydroxy groups was achieved via the 4,6-O-benzylidenation of the glucose moiety from its TMS ethers. The dimeric cyclization of the seco acids under control of reaction concentration afforded the desired lactide without using KH. Our convergent synthetic method was successfully applied to direct installation of side chains to the lactide by cross metathesis to synthesize fattiviracin derivatives. We achieved improvements to the reported method with respect to: (1) synthesis of a convergent synthetic intermediate; (2) stereoselectivity in glycosylation; and (3) establishment of a low cost route suitable for large scale synthesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.007