phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-mannopyranoside | 1158840-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-mannopyranoside
• CAS: 1158840-58-4
• 化学式: C₁₈H₂₆O₇S
• 分子量: 386.466
• InChiKey: LKDBGATZWLGSIW-AXSMETJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.61
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-mannopyranoside 、 叔丁基二甲基氯硅烷 在 吡啶 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Stereoselectivity of glycosylations of conformationally restricted mannuronate esters

  摘要：

  Glycosidation of conformationally unrestricted mannuronate ester donors proceeds in a highly P-selective fashion, whereas condensations of mannuronate ester donors, which are con formationally constrained by a 3,4-butanedimethylacetal or a 2,3-isopropylidene function, provide a-selective products. We hypothesize that the difference in stereochemical outcome of these condensations results from the different conformations of the product forming oxacarbenium intermediate. The formation of the beta-linked products from the flexible mannuronates is thought to originate from the most favorable H-3(4) oxacarbenium ion, which is not accessible from the conformationally restrained donors. Although an a-triflate intermediate is formed upon activation of the 3,4-butanedimethylacetal protected mannuronate ester thio donor, this is not the product forming intermediate. The anomeric triflate serves as a reservoir for the H-4(3) oxacarbenium ion, which is glycosidated to provide the a-linked mannuronates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.067
• 作为产物：
  描述：

  甲醇 、 phenyl 1-thio-β-D-mannopyranoside 、 2,3-丁二酮 在 camphor-10-sulfonic acid 、 原甲酸三甲酯 作用下， 以76%的产率得到phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  Stereoselectivity of glycosylations of conformationally restricted mannuronate esters

  摘要：

  Glycosidation of conformationally unrestricted mannuronate ester donors proceeds in a highly P-selective fashion, whereas condensations of mannuronate ester donors, which are con formationally constrained by a 3,4-butanedimethylacetal or a 2,3-isopropylidene function, provide a-selective products. We hypothesize that the difference in stereochemical outcome of these condensations results from the different conformations of the product forming oxacarbenium intermediate. The formation of the beta-linked products from the flexible mannuronates is thought to originate from the most favorable H-3(4) oxacarbenium ion, which is not accessible from the conformationally restrained donors. Although an a-triflate intermediate is formed upon activation of the 3,4-butanedimethylacetal protected mannuronate ester thio donor, this is not the product forming intermediate. The anomeric triflate serves as a reservoir for the H-4(3) oxacarbenium ion, which is glycosidated to provide the a-linked mannuronates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.067