[(2R,3R,4S,5S,6S)-4,5-dibenzoyloxy-6-[[dimethoxy(oxido)phosphaniumyl]methyl]-3-hydroxyoxan-2-yl]methyl benzoate | 363619-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6S)-4,5-dibenzoyloxy-6-[[dimethoxy(oxido)phosphaniumyl]methyl]-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 363619-58-3
• 化学式: C₃₀H₃₁O₁₁P
• 分子量: 598.543
• InChiKey: ZVKQQQJWZXZBRS-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6S)-4,5-dibenzoyloxy-6-[[dimethoxy(oxido)phosphaniumyl]methyl]-3-hydroxyoxan-2-yl]methyl benzoate 在 2,4,6-三甲基吡啶 、 三甲基溴硅烷 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  Allyl 4,6-di-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside 在 palladium dihydroxide potassium tert-butylate 、 氢气 、 溶剂黄146 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 4.83h， 生成 [(2R,3R,4S,5S,6S)-4,5-dibenzoyloxy-6-[[dimethoxy(oxido)phosphaniumyl]methyl]-3-hydroxyoxan-2-yl]methyl benzoate
  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 β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania
  作者：Vladimir S Borodkin、Michael A.J Ferguson、Andrei V Nikolaev

  DOI：10.1016/s0040-4039(01)00961-3

  日期：2001.7

  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.