(2S,3S,4R,5R,6S)-2-(dimethoxyphosphorylmethyl)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol | 144668-22-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6S)-2-(dimethoxyphosphorylmethyl)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
• CAS: 144668-22-4
• 化学式: C₃₀H₃₇O₈P
• 分子量: 556.593
• InChiKey: MOAMCXJAOKYYHE-VGYFXUJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6S)-2-(dimethoxyphosphorylmethyl)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol 在 palladium on activated charcoal sodium tetrahydroborate 、 hydrido(triphenylphosphine)copper(I) hexamer 、 氢气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 、 水 为溶剂， -77.0~65.0 ℃ 、101.33 kPa 条件下， 反应 54.5h， 生成 1L-(1,2,3/4,5)-1-C-Methyl-2,3,4,5-cyclohexanetetrol
  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：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 乙酸酐 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2S,3S,4R,5R,6S)-2-(dimethoxyphosphorylmethyl)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
  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

文献信息

• Direct Synthesis of the Isosteric Phosphono Analogues of α-L-Rhamnose 1-Phosphate and β-L-Fucose 1-Phosphate
  作者：Laura Cipolla、Barbara La Ferla、Luigi Panza、Francesco Nicotra

  DOI：10.1080/07328309808001879

  日期：1998.9.1

  The isosteric phosphono analogue of alpha-L-rhamnose 1-phosphate has been stereoselectively synthesized by reaction of 2,3,5-tri-O-benzyl-L-rhamnose with tetraethyl methylenediphosphonate and sodium hydride in diglyme, followed by deprotection with iodotrimethylsilane. To synthesize stereoselectively the isosteric phosphono analogue of beta-L-fucose 1-phosphate, 2,3,5- tri-O-benzyl-L-fuconolactone was treated with lithiated dimethyl methylenephosphonate, and the 3,4,5-tri-O-benzyl-1,7-dideoxy-1-(phospho dimethyl)-L-galactoheptulopyranose obtained was stereoselectively reduced with triethylsilane and boron trifluoride etherate to afford the dimethyl (2,3,4-tri-O-benzyl-beta-L fucopyranosyl)methanephosphonate which was finally deprotected with iodotrimethylsilane.