Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-1-thio-L-glycero-α-D-manno-heptopyranoside | 140209-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-1-thio-L-glycero-α-D-manno-heptopyranoside
• CAS: 140209-76-3
• 化学式: C₂₆H₃₄O₆S
• 分子量: 474.618
• InChiKey: KMJZLGKZRBDYRU-ZWYIGRMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-1-thio-L-glycero-α-D-manno-heptopyranoside 、 per-O-benzoyllactosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到Ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-1-thio-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

  摘要：

  The synthesis of methyl(ethyl) 2-thio-KDO (i.e. 1, 2, 5, 7 and 10) and ethyl 1-thio-LD-Hepp (i.e. 26 and 43) derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/IFOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer L-alpha-D-Hepp-(1 --> 5)-alpha-KDO-2-O-(CH2)3NH2 (37) and tetramer beta-D-Galp-(1 --> 4)-beta-D-Glep-(1 --> 4)-L-alpha-D-Hepp-(1 -->5)-alpha-KDO-2-O-(CH2)3NH2 (47).

  DOI：

  10.1016/s0040-4020(01)88191-6
• 作为产物：
  描述：

  Ethyl 2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside 在 水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-1-thio-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

  摘要：

  The synthesis of methyl(ethyl) 2-thio-KDO (i.e. 1, 2, 5, 7 and 10) and ethyl 1-thio-LD-Hepp (i.e. 26 and 43) derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/IFOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer L-alpha-D-Hepp-(1 --> 5)-alpha-KDO-2-O-(CH2)3NH2 (37) and tetramer beta-D-Galp-(1 --> 4)-beta-D-Glep-(1 --> 4)-L-alpha-D-Hepp-(1 -->5)-alpha-KDO-2-O-(CH2)3NH2 (47).

  DOI：

  10.1016/s0040-4020(01)88191-6