phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[3-O-(p-nitrobenzoyl)-β-D-olivopyranosyl]-β-D-olivopyranoside | 1030632-39-3

• 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-(tert-butyldimethylsilyl)-4-O-[3-O-(p-nitrobenzoyl)-β-D-olivopyranosyl]-β-D-olivopyranoside
• 英文别名: [(2R,3R,4R,6S)-6-[(2R,3R,4R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-phenylmethoxyoxan-3-yl]oxy-3-hydroxy-2-methyloxan-4-yl] 4-nitrobenzoate
• CAS: 1030632-39-3
• 化学式: C₃₂H₄₅NO₁₀Si
• 分子量: 631.796
• InChiKey: ZHOSTHJPADFXQW-UVYHUSEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[3-O-(p-nitrobenzoyl)-β-D-olivopyranosyl]-β-D-olivopyranoside 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[3-O-(p-nitrobenzoyl)-4-O-(tert-butyldimethylsilyl)-β-D-olivopyranosyl]-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：

  phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[2,6-dideoxy-β-D-ribo-hexopyranosyl]-β-D-olivopyranoside 、 对硝基苯甲酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[3-O-(p-nitrobenzoyl)-β-D-olivopyranosyl]-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