3-O-(6-O-tert-butyldimethylsilyl-2,3,5-tri-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol | 1236037-93-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-(6-O-tert-butyldimethylsilyl-2,3,5-tri-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol
• CAS: 1236037-93-6
• 化学式: C₆₄H₁₀₂O₁₀Si
• 分子量: 1059.59
• InChiKey: ARCZKFDRYMXZHI-XJXJQOQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.36
• 重原子数：
  75.0
• 可旋转键数：
  43.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-O-(6-O-tert-butyldimethylsilyl-2,3,5-tri-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以76%的产率得到3-O-(2,3,5-tri-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of the lipoteichoic acid of the Streptococcus species DSM 8747

  摘要：

  The lipoteichoic acid (LTA) of the Streptococcus species DSM 8747 consists of a beta-D-galactofuranosyl diacylglycerol moiety (with different acyl groups) that is linked via 6-O to a poly(glycerophosphate) backbone; about 30% of the glycerophosphate moieties carry at 2-O hydrolytically labile D-alanyl residues. As typical LTA for this array of compounds LTA 1a was synthesized. To this end, from D-galactose the required galactofuranosyl building block 5 was obtained. The anomeric stereocontrol in the glycosylation step with 1,2-O-cyclohexylidene-sn-glycerol (4) was based on anchimeric assistance, thus finally leading to the unprotected core glycolipid 16. Regioselective protection and deprotection procedures permitted the defined attachment of the pentameric glycerophosphate 3 to the 6-hydroxy group of the galactose residue. Introduction of four D-alanyl residues led after global deprotection and purification to target molecule 1a possessing on average about two D-alanyl residues at 2-O of the pentameric glycerophosphate backbone, thus being in close accordance with the structure of the natural material. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.04.006
• 作为产物：
  描述：

  3-O-(6-O-tert-butyldimethylsilyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到3-O-(6-O-tert-butyldimethylsilyl-2,3,5-tri-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of the lipoteichoic acid of the Streptococcus species DSM 8747

  摘要：

  The lipoteichoic acid (LTA) of the Streptococcus species DSM 8747 consists of a beta-D-galactofuranosyl diacylglycerol moiety (with different acyl groups) that is linked via 6-O to a poly(glycerophosphate) backbone; about 30% of the glycerophosphate moieties carry at 2-O hydrolytically labile D-alanyl residues. As typical LTA for this array of compounds LTA 1a was synthesized. To this end, from D-galactose the required galactofuranosyl building block 5 was obtained. The anomeric stereocontrol in the glycosylation step with 1,2-O-cyclohexylidene-sn-glycerol (4) was based on anchimeric assistance, thus finally leading to the unprotected core glycolipid 16. Regioselective protection and deprotection procedures permitted the defined attachment of the pentameric glycerophosphate 3 to the 6-hydroxy group of the galactose residue. Introduction of four D-alanyl residues led after global deprotection and purification to target molecule 1a possessing on average about two D-alanyl residues at 2-O of the pentameric glycerophosphate backbone, thus being in close accordance with the structure of the natural material. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.04.006