[(2S,3S,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-tribenzoyloxyoxan-2-yl]oxy-3,4-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]methylphosphonic acid | 493012-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-tribenzoyloxyoxan-2-yl]oxy-3,4-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]methylphosphonic acid
• CAS: 493012-77-4
• 化学式: C₅₇H₅₁O₂₀P
• 分子量: 1086.99
• InChiKey: SIMHJFUHHWMKQY-JDAHMKTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  78
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  275
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-tribenzoyloxyoxan-2-yl]oxy-3,4-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]methylphosphonic acid 在 sodium methylate N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 36.0h， 生成 dec-9-enoxy-[[(2S,3S,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl]phosphinate;triethylazanium
  参考文献：
  名称：

  Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

  摘要：

  An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00961-3
• 作为产物：
  描述：

  Allyl 4,6-di-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside 在 palladium dihydroxide 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 、 potassium tert-butylate 、 氢气 、 高氯酸,吡啶 、 溶剂黄146 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 20.33h， 生成 [(2S,3S,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-tribenzoyloxyoxan-2-yl]oxy-3,4-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]methylphosphonic acid
  参考文献：
  名称：

  Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

  摘要：

  An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00961-3

文献信息

• Synthesis of oligomeric phosphono analogues of Leishmania lipophosphoglycan fragments
  作者：Vladimir S. Borodkin、Fiona C. Milne、Michael A.J. Ferguson、Andrei V. Nikolaev

  DOI：10.1016/s0040-4039(02)01588-5

  日期：2002.10

  A set of isosteric phosphono (C-glycoside) analogues of Leishmania lipophosphoglycan fragments have been synthesised by making use of a sequence of uniformly stereoselective glycosylation reactions of phosphono-oligosaccharide glycosyl acceptors with phosphono-oligosaccharide thioglycosides.

  利什曼原虫脂磷酸糖片段的一组等排膦酰基（C-糖苷）类似物已通过利用膦酰基-寡糖糖基受体与膦酰基-低聚糖硫糖苷的均匀立体选择性糖基化反应序列而合成。