15-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-pentadecanoic acid methyl ester | 918298-77-8

• 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: 15-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-pentadecanoic acid methyl ester
• 英文别名: methyl 15-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypentadecanoate
• CAS: 918298-77-8
• 化学式: C₂₈H₅₂O₁₃
• 分子量: 596.713
• InChiKey: NJTWJMDCHJZOLX-CWBGAEIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  41
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  15-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-pentadecanoic acid methyl ester 在 Novozym-435 molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以75%的产率得到(1S,3R,4R,5S,6S,7R,26R,28R,29R,30R)-4,5,6,29,30-Pentahydroxy-28-hydroxymethyl-2,9,25,27,31-pentaoxa-tricyclo[24.2.2.1^3,7]hentriacontan-10-one
  参考文献：
  名称：

  Synthesis of glycolipid analogs via highly regioselective macrolactonization catalyzed by lipase

  摘要：

  Highly regioselective lipase catalyzed macrolactonization has been used in synthesizing first feedstock based glycolipid analogs. These macrolides containing common disaccharides maltose (4-O-alpha-D-glucopyranosyl-beta-D-glucose) and melibiose (6-O-alpha-D-galactopyranosyl-beta-D-glucose) were synthesized by employing chemoenzymatic methodologies. Maltose and Melibiose were coupled with methyl 15-hydroxy pentadecanoate and then subjected to a highly regioselective macrolactonization at the C-6" position using Candida antarctica lipase-B to yield the desired products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.041
• 作为产物：
  描述：

  环十五内酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 15-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-pentadecanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of glycolipid analogs via highly regioselective macrolactonization catalyzed by lipase

  摘要：

  Highly regioselective lipase catalyzed macrolactonization has been used in synthesizing first feedstock based glycolipid analogs. These macrolides containing common disaccharides maltose (4-O-alpha-D-glucopyranosyl-beta-D-glucose) and melibiose (6-O-alpha-D-galactopyranosyl-beta-D-glucose) were synthesized by employing chemoenzymatic methodologies. Maltose and Melibiose were coupled with methyl 15-hydroxy pentadecanoate and then subjected to a highly regioselective macrolactonization at the C-6" position using Candida antarctica lipase-B to yield the desired products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.041

文献信息

• Synthesis of glycolipid analogs via highly regioselective macrolactonization catalyzed by lipase
  作者：Kirpal S. Bisht、Surbhi Bhatt、Kirankirti Muppalla

  DOI：10.1016/j.tetlet.2006.10.041

  日期：2006.12

  Highly regioselective lipase catalyzed macrolactonization has been used in synthesizing first feedstock based glycolipid analogs. These macrolides containing common disaccharides maltose (4-O-alpha-D-glucopyranosyl-beta-D-glucose) and melibiose (6-O-alpha-D-galactopyranosyl-beta-D-glucose) were synthesized by employing chemoenzymatic methodologies. Maltose and Melibiose were coupled with methyl 15-hydroxy pentadecanoate and then subjected to a highly regioselective macrolactonization at the C-6" position using Candida antarctica lipase-B to yield the desired products. (c) 2006 Elsevier Ltd. All rights reserved.