phenylmethyl 3-O-(p-nitrobenzoyl)-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-olivopyranoside | 1030632-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylmethyl 3-O-(p-nitrobenzoyl)-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-olivopyranoside
• 英文别名: [(2R,3R,4R,6R)-2-methyl-3-[[(2R,6R)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-6-phenylmethoxyoxan-4-yl] 4-nitrobenzoate
• CAS: 1030632-19-9
• 化学式: C₂₆H₂₇NO₉
• 分子量: 497.502
• InChiKey: RCRDUNCZEOOPMN-NGGMLEQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenylmethyl 3-O-(p-nitrobenzoyl)-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-olivopyranoside 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到phenylmethyl 3-O-(p-nitrobenzoyl)-4-O-[(2R,6R)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yl]-β-D-olivopyranoside
  参考文献：
  名称：

  De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E

  摘要：

  A highly enantio- and diastereoselective synthesis of alpha-L-rhodinose, beta-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into ant 1,2-diol.

  DOI：

  10.1021/ol800697k
• 作为产物：
  描述：

  tert-butyl ((2S,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 、 phenylmethyl 3-O-(p-nitrobenzoyl)-β-D-olivopyranoside 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到phenylmethyl 3-O-(p-nitrobenzoyl)-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-olivopyranoside
  参考文献：
  名称：

  De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E

  摘要：

  A highly enantio- and diastereoselective synthesis of alpha-L-rhodinose, beta-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into ant 1,2-diol.

  DOI：

  10.1021/ol800697k

文献信息

• De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E
  作者：Maoquan Zhou、George A. O’Doherty

  DOI：10.1021/ol800697k

  日期：2008.6.5

  A highly enantio- and diastereoselective synthesis of alpha-L-rhodinose, beta-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into ant 1,2-diol.