| 1236162-72-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• CAS: 1236162-72-3
• 化学式: C₁₂₂H₁₆₅O₃₅P₅
• 分子量: 2346.5
• InChiKey: SQJVONIKKGTUMM-FHTLDVKZSA-N

反应信息

• 作为反应物：
  描述：

  N-Cbz-D-alanine triethylammonium salt 、 在 N-甲基咪唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以74%的产率得到
  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：

  在 ammonium cerium (IV) nitrate 、 水 作用下， 以 甲苯 、 乙腈 为溶剂， 以85%的产率得到
  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