N-[(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((E)-propenyl)-tetrahydro-pyran-3-yl]-acetamide | 578729-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((E)-propenyl)-tetrahydro-pyran-3-yl]-acetamide
• 英文别名: N-[(2S,3S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[(E)-prop-1-enyl]oxan-3-yl]acetamide
• CAS: 578729-63-2
• 化学式: C₃₂H₃₇NO₅
• 分子量: 515.649
• InChiKey: QQOYUASBCMRJQT-VGZGBUJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((E)-propenyl)-tetrahydro-pyran-3-yl]-acetamide 在 sodium chlorite 、 sodium periodate 、 四氧化锇 、 2-甲基-2-丁烯 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 生成 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid
  参考文献：
  名称：

  Synthesis of α- and β-C-glycosides of N-acetylglucosamine

  摘要：

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00818-9
• 作为产物：
  描述：

  5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol 在 甲醇 、 (Ph₂Me)2IrCOD*PF₆ 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-[(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((E)-propenyl)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Synthesis of α- and β-C-glycosides of N-acetylglucosamine

  摘要：

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00818-9

文献信息

• Synthesis of α- and β-C-glycosides of N-acetylglucosamine
  作者：Glenn J. McGarvey、Frank W. Schmidtmann、Tyler E. Benedum、Darin E. Kizer

  DOI：10.1016/s0040-4039(03)00818-9

  日期：2003.5

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.