tert-butyl (ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate | 311797-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate
• CAS: 311797-18-9
• 化学式: C₃₃H₄₀O₆S
• 分子量: 564.743
• InChiKey: RRMPTSBICRDAPX-UNOUFDOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.0h， 生成 methyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-1-硫代-Β-D-乙基半乳糖苷 在 吡啶 、 重铬酸吡啶 、 甲酸 、 水 、 sodium methylate 、 乙酸酐 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 tert-butyl (ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125