Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester | 419549-59-0

• 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: Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester
• CAS: 419549-59-0
• 化学式: C₃₄H₄₁N₃O₇
• 分子量: 603.715
• InChiKey: UKXIUHPKAFRVGE-BJPULKCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  44.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121.21
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester 在 4 A molecular sieve 、 sodium methylate 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 13.17h， 生成 5-azidopentyl (4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni

  摘要：

  The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)- [alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

  DOI：

  10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c
• 作为产物：
  描述：

  ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 4 A molecular sieve 、 对甲苯磺酸 、 溶剂黄146 、 三氟甲烷磺酸甲酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.43h， 生成 Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni

  摘要：

  The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)- [alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

  DOI：

  10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c