2'-(benzyloxycarbonyl)benzyl β-D-galactofuranoside | 911371-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl β-D-galactofuranoside
• 英文别名: benzyl 2-[[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxymethyl]benzoate
• CAS: 911371-41-0
• 化学式: C₂₁H₂₄O₈
• 分子量: 404.417
• InChiKey: PFMKDPDLNJNZNZ-BKZNIZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl β-D-galactofuranoside 在 palladium on activated charcoal 乙酸铵 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2'-carboxybenzyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  Total Synthesis of Agelagalastatin

  摘要：

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.

  DOI：

  10.1021/ol061444o
• 作为产物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到2'-(benzyloxycarbonyl)benzyl β-D-galactofuranoside
  参考文献：
  名称：

  Total Synthesis of Agelagalastatin

  摘要：

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.

  DOI：

  10.1021/ol061444o

文献信息

• Chemical Synthesis of Cyclic Galactooligofuranosides Isolated from Enzymatic Degradation Products of Cell Wall Arabinogalactan of <i>Mycobacterium tuberculosis</i>
  作者：Kwan Soo Kim、Bo-Young Lee、Sung Ho Yoon、Hyo Jin Jeon、Ju Yuel Baek、Kyu-Sung Jeong

  DOI：10.1021/ol800530u

  日期：2008.6.1

  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.