methyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-L-glycero-α-D-gluco-heptopyranoside | 352547-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-L-glycero-α-D-gluco-heptopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-2-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]acetamide
• CAS: 352547-23-0
• 化学式: C₂₄H₃₁NO₇
• 分子量: 445.513
• InChiKey: CEECNAPBXRUYAT-RFZFRQTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-L-glycero-α-D-gluco-heptopyranoside 在 吡啶 作用下， 生成 methyl 2-acetamido-6,7-di-O-acetyl-3,4-di-O-benzyl-2-deoxy-L-glycero-α-D-gluco-heptopyranoside
  参考文献：
  名称：

  Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride

  摘要：

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00078-7
• 作为产物：
  描述：

  methyl 2-acetamido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranoside 在 sodium acetate 、 戴斯-马丁氧化剂 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.28h， 生成 methyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-L-glycero-α-D-gluco-heptopyranoside
  参考文献：
  名称：

  Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride

  摘要：

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00078-7

文献信息

• Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride
  作者：Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0008-6215(01)00078-7

  日期：2001.5

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.