(3aS,4S,6R,7R,7aS)-4-[[dimethoxy(oxido)phosphaniumyl]methyl]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran | 363619-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6R,7R,7aS)-4-[[dimethoxy(oxido)phosphaniumyl]methyl]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 363619-54-9
• 化学式: C₂₆H₃₅O₈P
• 分子量: 506.533
• InChiKey: ANIPSQSLUIJDJW-JYSSUKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,7R,7aS)-4-[[dimethoxy(oxido)phosphaniumyl]methyl]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran 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 、 氢气 、 高氯酸,吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.0h， 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 potassium tert-butylate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.33h， 生成 (3aS,4S,6R,7R,7aS)-4-[[dimethoxy(oxido)phosphaniumyl]methyl]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
  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.