phenyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside | 190782-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylselanyloxan-3-amine
• CAS: 190782-03-7
• 化学式: C₃₃H₃₅NO₄Se
• 分子量: 588.605
• InChiKey: VOPRDCKUMKODBD-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 在 叔丁基过氧化氢 、 三乙胺 作用下， 以 四氢呋喃 、 正辛烷 为溶剂， 反应 98.0h， 生成 C₆₁H₆₄NO₁₀PSe
  参考文献：
  名称：

  通过暂时的磷酰胺连接自由基介导的含C-二糖的合成

  摘要：

  所述Ç -disaccharide {α-d-的GalNAc-C-（1→）-β-d-GLC-OME}及其interglycosidicβ端基异构体是由苯基的自由基偶联合成到甲基，其通过磷酰氨系绳临时连接。类似的反应用甲基进行，以产生两个密切相关的α-OME Ç -disaccharides。

  DOI：

  10.1016/s0957-4166(97)00141-9
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 lithium aluminium tetrahydride 、 sodium azide 、 碘苯二乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.08h， 生成 phenyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  通过暂时的磷酰胺连接自由基介导的含C-二糖的合成

  摘要：

  所述Ç -disaccharide {α-d-的GalNAc-C-（1→）-β-d-GLC-OME}及其interglycosidicβ端基异构体是由苯基的自由基偶联合成到甲基，其通过磷酰氨系绳临时连接。类似的反应用甲基进行，以产生两个密切相关的α-OME Ç -disaccharides。

  DOI：

  10.1016/s0957-4166(97)00141-9

文献信息

• Convenient Preparation of Perbenzylated 2-Azido and 2-<i>N</i>-Acetylamino-2-Deoxy-<scp>d</scp>-Hexono-1,5-Lactones by Oxidation of the Corresponding Lactols
  作者：Ebtissam Ayadi、Stanislas Czernecki、Juan Xie

  DOI：10.1080/07328309608005438

  日期：1996.2

  2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).
• Stereocontrolled synthesis of 2-amino-2-deoxy-α-d-c-glycopyranosides by radical cyclization reactions
  作者：Stanislas Czernecki、Ebtissam Ayadi、Juan Xie

  DOI：10.1016/s0040-4039(96)02153-3

  日期：1996.12

  Radical cyclization of phenyl 2-N-allylamino-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-1-seleno galacto and gluco pyranosides afforded alpha-D-C-glycopyranosides with high stereoselectivity involving a 5-exo-trig mechanism. Copyright (C) 1996 Elsevier Science Ltd
• Radical mediated synthesis of containing C-disaccharides via a temporary phosphoramidic connection
  作者：Gilles Rubinstenn、Jacques Esnault、Jean-Maurice Mallet、Pierre Sinaÿ

  DOI：10.1016/s0957-4166(97)00141-9

  日期：1997.4

  The C-disaccharide α-d-GalNAc-C-(1→)-β-d-Glc-OMe} and its interglycosidic β anomer were synthesized by radical coupling of phenyl onto methyl , which are temporarily connected through a phosphoramido tether. A similar reaction was performed with methyl to produce the two closely related α-OMe C-disaccharides.

  所述Ç -disaccharide α-d-的GalNAc-C-（1→）-β-d-GLC-OME}及其interglycosidicβ端基异构体是由苯基的自由基偶联合成到甲基，其通过磷酰氨系绳临时连接。类似的反应用甲基进行，以产生两个密切相关的α-OME Ç -disaccharides。