phenylmethyl 4-O-[(2S,6R)-3,6-dihydro-6-methyl-2H-pyran-2-yl]-β-D-olivopyranoside | 1030632-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenylmethyl 4-O-[(2S,6R)-3,6-dihydro-6-methyl-2H-pyran-2-yl]-β-D-olivopyranoside
• CAS: 1030632-29-1
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: BROUPVAYFVVKDQ-UPPPXSOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenylmethyl 4-O-[(2S,6R)-3,6-dihydro-6-methyl-2H-pyran-2-yl]-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72%的产率得到phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[(2S,6R)-3,6-dihydro-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：

  phenylmethyl 3-O-(p-nitrobenzoyl)-4-O-[(2S,6R)-3,6-dihydro-6-methyl-2H-pyran-2-yl]-β-D-olivopyranoside 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以98%的产率得到phenylmethyl 4-O-[(2S,6R)-3,6-dihydro-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