2'-(benzyloxycarbonyl)benzyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside | 1033706-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside
• CAS: 1033706-55-6
• 化学式: C₄₂H₃₈O₁₀
• 分子量: 702.758
• InChiKey: DNIFWMWDZBMFJB-PPUGHRORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  52.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  126.82
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside 、 2'-carboxybenzyl 2,3,5-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-galactofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到2'-(benzyloxycarbonyl)benzyl (2,3,5-tri-O-benzoyl-6-O-t-buthyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  Chemical Synthesis of Cyclic Galactooligofuranosides Isolated from Enzymatic Degradation Products of Cell Wall Arabinogalactan of Mycobacterium tuberculosis

  摘要：

  Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1 -> 5)-,beta- and (1 -> 6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular,cyclooligornerization of the (1 -> 6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.

  DOI：

  10.1021/ol800530u
• 作为产物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 2,3-di-O-benzoyl-β-D-galactofuranoside 、 氯化苄 在 二正丁基氧化锡 、 四丁基碘化铵 作用下， 以 苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以86%的产率得到2'-(benzyloxycarbonyl)benzyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  Chemical Synthesis of Cyclic Galactooligofuranosides Isolated from Enzymatic Degradation Products of Cell Wall Arabinogalactan of Mycobacterium tuberculosis

  摘要：

  Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1 -> 5)-,beta- and (1 -> 6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular,cyclooligornerization of the (1 -> 6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.

  DOI：

  10.1021/ol800530u

文献信息

• Synthesis of a tetrasaccharide phosphate from the linkage region of the arabinogalactan–peptidoglycan complex in the mycobacterial cell wall
  作者：Yong Joo Lee、Dinanath Baburao Fulse、Kwan Soo Kim

  DOI：10.1016/j.carres.2008.05.009

  日期：2008.7

  The synthesis of dibenzyl 6-O-naphthylmethyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 -> 5)-2,3-di-O-benzoyl-6-O-benzyl- beta-D-galactofuranosyl-(1 -> 4)-3-O-benzyl-2-O-pivaloyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-4,6-di-O-benzoyl-alpha-glucopyranosyl phosphate (1), a protected form of the tetrasaccharide phosphate of the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall, has been accomplished. Key steps include the coupling of four monosaccharide building blocks with complete stereoselectivity by glycosylations employing thioglycosides, 2'-carboxybenzyl glycosides, and glycosyl fluorides as glycosyl donors. The alpha-glycosyl phosphate linkage was also stereoselectively elaborated by reaction of a tetrasaccharide hermacetal with tetrabenzyl pyrophosphate in the presence of a base. (C) 2008 Elsevier Ltd. All rights reserved.