methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside | 236424-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-ethenyl-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 236424-93-4
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: YPZMWTRIUCPZTE-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside 在 Grubbs catalyst first generation sodium hydride 、 mineral oil 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 (1R,6R,8S,9R,10S)-9,10-bis(benzyloxy)-8-methoxy-2,7-dioxabicyclo[4.4.0]dec-4-ene
  参考文献：
  名称：

  A convenient route to cis- and trans-fused bicyclic ethers by ruthenium mediated ring-closing metathesis of diene and enyne carbohydrate derivatives

  摘要：

  A general approach towards the construction of highly functionalised pyranopyran and pyranofuran systems via Grubbs [Ru] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-propargyl functions on monosaccharide scaffolds is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00296-3
• 作为产物：
  描述：

  (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran 在 camphor-10-sulfonic acid 、 四丁基氟化铵 作用下， 以 甲醇 为溶剂， 生成 methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

  摘要：

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01617-9

文献信息

• A convenient route to cis- and trans-fused bicyclic ethers by ruthenium mediated ring-closing metathesis of diene and enyne carbohydrate derivatives
  作者：Michiel A. Leeuwenburgh、Camiel Kulker、Howard I. Duynstee、Herman S. Overkleeft、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(99)00296-3

  日期：1999.7

  A general approach towards the construction of highly functionalised pyranopyran and pyranofuran systems via Grubbs [Ru] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-propargyl functions on monosaccharide scaffolds is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Cross-metathesis and ring-closing metathesis of olefinic monosaccharides
  作者：Maarten H.D. Postema、Jared L. Piper

  DOI：10.1016/s0040-4039(02)01617-9

  日期：2002.9

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.