methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate | 347838-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate
• 英文别名: methyl (2S,3S,4R,5S,6R)-4-acetyloxy-5-(diacetylamino)-2-diethoxyphosphanyloxy-3-phenylselanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 347838-08-8
• 化学式: C₃₂H₄₄NO₁₆PSe
• 分子量: 808.632
• InChiKey: UPWBXTHFUZNGMV-NGKCABGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  51
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  206
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 1,2;3,4-di-O-isopropylidene-6-O-[methyl (5-acetamido-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosyl)onate]-α-D-galactopyranose
  参考文献：
  名称：

  A study of the donor properties of sialyl phosphites having an auxiliary 3-(S)-phenylseleno group

  摘要：

  Two phosphite sialyl donors, each having an auxiliary 3-(S)-phenylseleno group, were prepared and evaluated. The phenylseleno group was introduced via a new mode of generating phenylselenenic acid ('PhSeOH'). Although the sialyl donors provided fair yields (32-76%) of the desired sialosides in glycosylations of the reactive acceptor 1,2;3,4-di-O-isopropylidene-alpha -D-galactopyranose, no sialylated products could be obtained with less reactive accepters. The presence of a 5-N-acetylacetamido group on the phosphite sialyl donor did not appear to improve its sialylating capability. The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors alpha -nitrilium ion formation, seem to explain the unsuccessful sialylations of the less reactive accepters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00029-5
• 作为产物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate 在 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate
  参考文献：
  名称：

  A study of the donor properties of sialyl phosphites having an auxiliary 3-(S)-phenylseleno group

  摘要：

  Two phosphite sialyl donors, each having an auxiliary 3-(S)-phenylseleno group, were prepared and evaluated. The phenylseleno group was introduced via a new mode of generating phenylselenenic acid ('PhSeOH'). Although the sialyl donors provided fair yields (32-76%) of the desired sialosides in glycosylations of the reactive acceptor 1,2;3,4-di-O-isopropylidene-alpha -D-galactopyranose, no sialylated products could be obtained with less reactive accepters. The presence of a 5-N-acetylacetamido group on the phosphite sialyl donor did not appear to improve its sialylating capability. The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors alpha -nitrilium ion formation, seem to explain the unsuccessful sialylations of the less reactive accepters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00029-5