methyl 2-acetamido-3,4-di-O-benzyl-2,7-dideoxy-7-(phenydimethylsilyl)-L-glycero-α-D-gluco-heptopyranoside | 352547-22-9

• 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-2,7-dideoxy-7-(phenydimethylsilyl)-L-glycero-α-D-gluco-heptopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-6-[(1R)-2-[dimethyl(phenyl)silyl]-1-hydroxyethyl]-2-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]acetamide
• CAS: 352547-22-9
• 化学式: C₃₂H₄₁NO₆Si
• 分子量: 563.766
• InChiKey: YAXPHBIHEQNFFG-VGCNAVONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3,4-di-O-benzyl-2,7-dideoxy-7-(phenydimethylsilyl)-L-glycero-α-D-gluco-heptopyranoside 在 sodium acetate 、 potassium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以50%的产率得到1,3-di-[methyl 2-acetamido-3,4-di-O-benzyl-2,7-dideoxy-L-glycero-α-D-gluco-heptopyranosi-7-yl]-1,1,3,3-tetramethyl-disiloxane
  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 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.28h， 生成 methyl 2-acetamido-3,4-di-O-benzyl-2,7-dideoxy-7-(phenydimethylsilyl)-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.