phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[2,6-dideoxy-β-D-ribo-hexopyranosyl]-β-D-olivopyranoside | 1030632-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[2,6-dideoxy-β-D-ribo-hexopyranosyl]-β-D-olivopyranoside
• 英文别名: Dig(b1-4)[TBDMS(-3)]Oli(b)-O-Bn；(2R,3S,4S,6S)-6-[(2R,3R,4R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-phenylmethoxyoxan-3-yl]oxy-2-methyloxane-3,4-diol
• CAS: 1030632-35-9
• 化学式: C₂₅H₄₂O₇Si
• 分子量: 482.69
• InChiKey: WJLVVSOSUPVLCP-GZIMIAIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[(2S,6R)-3,6-dihydro-6-methyl-2H-pyran-2-yl]-β-D-olivopyranoside 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到phenylmethyl 3-O-(tert-butyldimethylsilyl)-4-O-[2,6-dideoxy-β-D-ribo-hexopyranosyl]-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.