dibenzyl [(1S,4R,5R,6S)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-yl] phosphate | 144668-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl [(1S,4R,5R,6S)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-yl] phosphate
• CAS: 144668-31-5
• 化学式: C₄₂H₄₃O₇P
• 分子量: 690.773
• InChiKey: DULAKMSSKPAIIT-CVGILMMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dibenzyl [(1S,4R,5R,6S)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-yl] phosphate 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(1S,4R,5R,6S)-4,5,6-trihydroxy-3-methylcyclohex-2-en-1-yl] hydrogen phosphate
  参考文献：
  名称：

  Synthesis of carbocyclic analogs of guanosine 5'-(.beta.-L-fucopyranosyl diphosphate) (GDP-fucose) as potential inhibitors of fucosyltransferases.

  摘要：

  Two carbocyclic analogues of GDP-fucose consisting of 5a-carba-beta-L-fucopyranose and its unsaturated counterpart have been synthesized as potential inhibitors of fucosyltransferases through the intramolecular Emmons-Horner-Wadsworth olefination of the 2,6-dioxo-phosphonate derivative, readily available from L-fucose, followed by chemo- and stereoselective reductions of the alpha,beta-unsaturated inosose intermediate, which are the critical steps.

  DOI：

  10.1021/jo00051a004
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-L-fuconolactone 在 四氮唑 、 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 8.75h， 生成 dibenzyl [(1S,4R,5R,6S)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-yl] phosphate
  参考文献：
  名称：

  Synthesis of carbocyclic analogs of guanosine 5'-(.beta.-L-fucopyranosyl diphosphate) (GDP-fucose) as potential inhibitors of fucosyltransferases.

  摘要：

  Two carbocyclic analogues of GDP-fucose consisting of 5a-carba-beta-L-fucopyranose and its unsaturated counterpart have been synthesized as potential inhibitors of fucosyltransferases through the intramolecular Emmons-Horner-Wadsworth olefination of the 2,6-dioxo-phosphonate derivative, readily available from L-fucose, followed by chemo- and stereoselective reductions of the alpha,beta-unsaturated inosose intermediate, which are the critical steps.

  DOI：

  10.1021/jo00051a004