Ethyl 2-O-benzoyl-3-O-methyl-1-thio-β-D-fucopyranoside | 179337-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2-O-benzoyl-3-O-methyl-1-thio-β-D-fucopyranoside
• CAS: 179337-22-5
• 化学式: C₁₆H₂₂O₅S
• 分子量: 326.414
• InChiKey: DRZKABPLMVBWQT-QUZFFSQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Ethyl 2-O-benzoyl-3-O-methyl-1-thio-β-D-fucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 叠氮化锂 、 三氟甲磺酸 、 4 A molecular sieve 、 硫化氢 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.58h， 生成 3-(Benzyloxycarbonylamino)propyl 2,4-di-O-benzoyl-3-O-[2-O-benzoyl-4-O-methyl-3-O-(4-amino-2-O-benzoyl-3-O-methyl-β-D-quinovopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Haptenic Trimers Corresponding to the Cell Wall Glycopeptidolipids ofMycobacterium AviumSerovar 12

  摘要：

  The preparation of the spacer-containing trimers 2, 3-aminopropyl 3-O-[4-O-Me-3-O-(4-N-D,L-lactoyl-3-O-Me-beta-D-Quip)-alpha-L-Rhap]-alpha-L-Rhap, derivatives of the antigenic determinant of the glycopeptidolipid from Mycobacterium avium serotype 12, are described. Thus, iodonium ion-mediated glycosylation of the spacer-containing acceptor 7 with ethyl 1-thio-rhamnopyranoside donor 10, followed try selective deprotection of the p-methoxybenzyl group of thus obtained 19 gave bis-rhamnopyranoside acceptor 20. Elongation of 20 with ethyl 4-azido-1-thio-beta-D-quinovopyranoside 18 and subsequent reduction of the azido function in 21 led to trimer 22. The amino group in 22 was coupled with both D- and L-lactic acid to give, after removal of the protective groups, trimers 2.

  DOI：

  10.1080/07328309608005677
• 作为产物：
  描述：

  ethyl 1-thio-α-L-rhamnopyranoside 、 碘甲烷 在 二正丁基氧化锡 、 cesium fluoride 作用下， 生成 Ethyl 2-O-benzoyl-3-O-methyl-1-thio-β-D-fucopyranoside
  参考文献：
  名称：

  Synthesis of Haptenic Trimers Corresponding to the Cell Wall Glycopeptidolipids ofMycobacterium AviumSerovar 12

  摘要：

  The preparation of the spacer-containing trimers 2, 3-aminopropyl 3-O-[4-O-Me-3-O-(4-N-D,L-lactoyl-3-O-Me-beta-D-Quip)-alpha-L-Rhap]-alpha-L-Rhap, derivatives of the antigenic determinant of the glycopeptidolipid from Mycobacterium avium serotype 12, are described. Thus, iodonium ion-mediated glycosylation of the spacer-containing acceptor 7 with ethyl 1-thio-rhamnopyranoside donor 10, followed try selective deprotection of the p-methoxybenzyl group of thus obtained 19 gave bis-rhamnopyranoside acceptor 20. Elongation of 20 with ethyl 4-azido-1-thio-beta-D-quinovopyranoside 18 and subsequent reduction of the azido function in 21 led to trimer 22. The amino group in 22 was coupled with both D- and L-lactic acid to give, after removal of the protective groups, trimers 2.

  DOI：

  10.1080/07328309608005677