methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate | 110390-66-4

• 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: methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate
• 英文别名: 1-methoxycarbonyl-3,4,6-tri-O-benzyl-D-glucal；3,4,6-tri-O-benzyl-1-methoxycarbonyl-D-glucal；methyl (2R,3S,4R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 110390-66-4
• 化学式: C₂₉H₃₀O₆
• 分子量: 474.554
• InChiKey: RSLMQJXSOYEDPI-KZQOYIJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate 在 盐酸 、 氢氧化钾 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 叔丁醇 为溶剂， 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 2-[(2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy]acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以82%的产率得到methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate
  参考文献：
  名称：

  深入研究碳水化合物衍生的α-烷氧基丙烯酸酯的闭环复分解：DAH，KDO和2-Deoxy-β-KDO的高效合成

  摘要：

  描述了通往DAH，KDO和2-deoxy-β-KDO的新颖，有效的合成途径。高度官能化的α-烷氧基丙烯酸酯片段的闭环复分解（RCM）导致了一系列合成上通用的氧杂环中间体。从可商购的被保护的糖开始，所得烯醇醚双键的进一步官能化和随后的脱保护以高的总收率提供了天然产物。

  DOI：

  10.1021/jo060913x

文献信息

• Crich, David; Ritchie, Timothy J., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 945 - 954
  作者：Crich, David、Ritchie, Timothy J.

  DOI：——

  日期：——
• Preparation and use of lithiated glycals: vinylic deprotonation versus tin-lithium exchange from 1-tributylstannyl glycals1
  作者：Patrick Lesimple、Jean-Marie Beau、Guy Jaurand、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)85432-5

  日期：1986.1
• 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：——
• CRICH, DAVID;RITCHIE, TIMOTHY J., J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 945-954
  作者：CRICH, DAVID、RITCHIE, TIMOTHY J.

  DOI：——

  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.