methyl 2-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranoside | 917591-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranoside
• 英文别名: Bz(-2)D-Araf(a1-5)[Bn(-2)][Bn(-3)]D-Araf(a1-5)[Bn(-2)][Bn(-3)]a-D-Araf1Me；[(2S,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-[[(2R,3R,4S,5S)-5-[[(2R,3R,4S,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxy]-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxy]oxolan-3-yl] benzoate
• CAS: 917591-15-2
• 化学式: C₅₁H₅₆O₁₄
• 分子量: 892.997
• InChiKey: GFTZFHFWSMXFDK-HHJVXDMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2R,3S,4R,5R)-4-benzyloxy-5-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester 、 methyl 2-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan

  摘要：

  Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-( 1,2- cis)- selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. beta-Selectivity was drastically enhanced by using donors protected with 3,5- TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.

  DOI：

  10.1021/ol062198j
• 作为产物：
  描述：

  p-cresyl 2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 methyl 2-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan

  摘要：

  Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-( 1,2- cis)- selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. beta-Selectivity was drastically enhanced by using donors protected with 3,5- TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.

  DOI：

  10.1021/ol062198j

文献信息

• Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan
  作者：Akihiro Ishiwata、Hiroko Akao、Yukishige Ito

  DOI：10.1021/ol062198j

  日期：2006.11.1

  Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-( 1,2- cis)- selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. beta-Selectivity was drastically enhanced by using donors protected with 3,5- TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.