methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate | 136305-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate
• 英文别名: methyl 4,5,7-tri-O-benzyl-α-D-gluco-2-heptulopyranosonate；methyl (2R,3R,4R,5R,6R)-2,3-dihydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-carboxylate
• CAS: 136305-59-4
• 化学式: C₂₉H₃₂O₈
• 分子量: 508.568
• InChiKey: VEEYPFTZUBYUMF-LJNCTHMASA-N

物化性质

• 沸点：
  623.5±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate 在 盐酸 、 氢氧化钾 作用下， 生成 3,4,6-tri-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranose
  参考文献：
  名称：

  Diastereoselective radical reactions : β-face selective quenching of the 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-d-glucopyranos-1-yl radical

  摘要：

  Pyrolysis of 3,4,6-tri-O-benzyl-1-carbomethoxy-1,2-dideoxy-1-phenylsulfonyl-D-glucopyranose provides the corresponding 1-carbomethoxyglucal which reacts with osmium tetroxide to form a gluco-diol. This diol is converted to an acetonide which is saponified and subjected to the Barton reductive decarboxylation procedure with exclusive quenching of the intermediate radical from the beta-face representing the first example of a reaction in which a glucopyranosyl radical is selectively quenched from this direction. An improved procedure for the preparation of 3,4,6-tri-O-benzyl-D-glucopyranose is presented.

  DOI：

  10.1016/s0040-4039(00)78786-7
• 作为产物：
  描述：

  methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate 在 吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 以92%的产率得到methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate
  参考文献：
  名称：

  Crich, David; Lim, Linda B. L., Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2209 - 2214

  摘要：

  DOI：

文献信息

• 10.1002/1099-0690(20021)2002:1<57::aid-ejoc57<3.0.co;2-h
  作者：Reiner, Martin、Stolz, Florian、Schmidt, Richard R.

  DOI：10.1002/1099-0690(20021)2002:1<57::aid-ejoc57<3.0.co;2-h

  日期：——
• Diastereoselective radical reactions : β-face selective quenching of the 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-d-glucopyranos-1-yl radical
  作者：David Crich、Linda B.L. Lim

  DOI：10.1016/s0040-4039(00)78786-7

  日期：1991.6

  Pyrolysis of 3,4,6-tri-O-benzyl-1-carbomethoxy-1,2-dideoxy-1-phenylsulfonyl-D-glucopyranose provides the corresponding 1-carbomethoxyglucal which reacts with osmium tetroxide to form a gluco-diol. This diol is converted to an acetonide which is saponified and subjected to the Barton reductive decarboxylation procedure with exclusive quenching of the intermediate radical from the beta-face representing the first example of a reaction in which a glucopyranosyl radical is selectively quenched from this direction. An improved procedure for the preparation of 3,4,6-tri-O-benzyl-D-glucopyranose is presented.
• Crich, David; Lim, Linda B. L., Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2209 - 2214
  作者：Crich, David、Lim, Linda B. L.

  DOI：——

  日期：——