(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-6-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• 化学式: C₃₈H₄₆O₁₀
• 分子量: 662.777
• InChiKey: CYOJEINROGHCGZ-UZCRRKBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2'-carboxybenzyl tri-O-benzyl-D-arabinofuranoside 、 双丙酮葡萄糖 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 、 (2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Acceptor-Dependent Stereoselective Glycosylation:  2‘-CB Glycoside-Mediated Direct β-d-Arabinofuranosylation and Efficient Synthesis of the Octaarabinofuranoside in Mycobacterial Cell Wall

  摘要：

  A reliable and generally applicable direct method for the stereoselective beta-arabinofuranosylation employing a 2'-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosyl acceptors is essential for the beta-stereoselectivity. The power of the present acceptor-dependent glycosylation method was demonstrated by the efficient synthesis of the octaarabinofuranoside in arabinogalactan and lipoarabinomannan found in mycobacterial cell wall.

  DOI：

  10.1021/ol0510668

文献信息

• Acceptor-Dependent Stereoselective Glycosylation:  2‘-CB Glycoside-Mediated Direct β-<scp>d</scp>-Arabinofuranosylation and Efficient Synthesis of the Octaarabinofuranoside in Mycobacterial Cell Wall
  作者：Yong Joo Lee、Kyunghoon Lee、Eun Hye Jung、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1021/ol0510668

  日期：2005.7.1

  A reliable and generally applicable direct method for the stereoselective beta-arabinofuranosylation employing a 2'-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosyl acceptors is essential for the beta-stereoselectivity. The power of the present acceptor-dependent glycosylation method was demonstrated by the efficient synthesis of the octaarabinofuranoside in arabinogalactan and lipoarabinomannan found in mycobacterial cell wall.