P¹-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) P¹-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) P²-[ethyl (3,6-anhydro-2-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octosyl)] methylenediphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: P¹-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) P¹-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) P²-[ethyl (3,6-anhydro-2-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octosyl)] methylenediphosphonate
• 英文别名: (1S,2R,6R,8R,9S)-8-[[[2-[(3aS,4R,6S,6aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethoxy-ethoxy-oxidophosphaniumyl]methyl-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-oxidophosphaniumyl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• 化学式: C₃₈H₆₄O₂₀P₂
• 分子量: 902.862
• InChiKey: DMWCMIKJHYLQAV-ZOTIQRTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  (1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) (1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) methylphosphonate 、 二氯磷酸乙酯 、 3,6-anhydro-2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-talo/galacto octitol 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 P¹-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) P¹-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) P²-[ethyl (3,6-anhydro-2-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octosyl)] methylenediphosphonate 、 P¹-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) P¹-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) P²-[ethyl (3,6-anhydro-2-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octosyl)] methylenediphosphonate
  参考文献：
  名称：

  One-Pot Carbanionic Synthesis of P¹_,P²-Diglycosyl, P¹,P¹,P²-Triglycosyl, and P¹,P¹,P²,P²-Tetraribosyl Methylenediphosphonates

  摘要：

  Novel lithiated carbanions derived from ethyl glycosyl- and diglycosyl methylphosphonates were used in a direct and convenient synthesis of P-1, P-2-diglycosyl, P-1, P-1, P-2-triglycosyl, and P-1, P-1, P-2, P-2- tetraribosyl methylenediphosphonates involving a one-pot methylidenediphosphonylation of sugars.

  DOI：

  10.1021/jo061087v