((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-acetic acid | 258854-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-acetic acid
• 英文别名: 2-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(trityloxymethyl)oxan-2-yl]oxyacetic acid
• CAS: 258854-16-9
• 化学式: C₄₈H₄₆O₈
• 分子量: 750.888
• InChiKey: WVUYEIOZGFUDSF-WKKVOTSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-O-(三乙基硅烷基)-10-去乙酰基浆果赤霉素III 、 ((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-acetic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-12-[2-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(trityloxymethyl)oxan-2-yl]oxyacetyl]oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Water Soluble Taxoids Bearing Sugar Moieties

  摘要：

  Synthesis and biological evaluation of a variety of water soluble taxoids with sugar moieties an described.

  DOI：

  10.3987/com-00-s(i)34
• 作为产物：
  描述：

  3-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-propane-1,2-diol 在 sodium chlorite 、 sodium periodate 作用下， 以 1,4-二氧六环 、 叔丁醇 为溶剂， 反应 15.0h， 生成 ((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-acetic acid
  参考文献：
  名称：

  A Practical Synthetic Method for a- and b-Glycosyloxyacetic Acids

  摘要：

  Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into alpha- and beta-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.

  DOI：

  10.3987/com-99-s43

文献信息

• A Practical Synthetic Method for a- and b-Glycosyloxyacetic Acids
  作者：Tadakatsu Mandai、Hiroshi Okumoto、Tetsuta Oshitari、Katsuyoshi Nakanishi、Katsuhiko Mikuni、Ko-ji Hara、Ko-zo Hara

  DOI：10.3987/com-99-s43

  日期：——

  Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into alpha- and beta-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.
• Synthesis and Biological Evaluation of Water Soluble Taxoids Bearing Sugar Moieties
  作者：Tadakatsu Mandai、Hiroshi Okumoto、Tetsuta Oshitari、Katsuyoshi Nakanishi、Katsuhiko Mikuni、Ko-ji Hara、Ko-zo Hara、Wakao Iwatani、Tetsuya Amano、Kosho Nakamura、Yoshinori Tsuchiya

  DOI：10.3987/com-00-s(i)34

  日期：——

  Synthesis and biological evaluation of a variety of water soluble taxoids with sugar moieties an described.