β-D-galactopyranose-6-O-trithiotriphosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranose-6-O-trithiotriphosphate
• 英文别名: (2R,3R,4S,5R,6R)-6-[[[dihydroxyphosphinothioyloxy(hydroxy)phosphinothioyl]oxy-hydroxyphosphinothioyl]oxymethyl]oxane-2,3,4,5-tetrol
• 化学式: C₆H₁₅O₁₂P₃S₃
• 分子量: 468.297
• InChiKey: GWPZNEPUPWJACT-XAXZFNGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  295
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  β-半乳糖苷酶 生成 β-D-galactopyranose-6-O-trithiotriphosphate
  参考文献：
  名称：

  Selective Diphosphorylation, Dithiodiphosphorylation, Triphosphorylation, and Trithiotriphosphorylation of Unprotected Carbohydrates and Nucleosides

  摘要：

  [GRAPHIC]Aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with diphosphitylarting and triphosphitylating reagents to yield the corresponding polymer-bound cliphosphitylating and triphosphitylating reagents, respectively. A number of unprotected carbohydrates and nucleosides were reacted with the polymer-bound reagents. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by removal of cyanoethoxy group with DBU and the acidic cleavage, respectively, afforded only one type of monosubstituted nucleoside and carbohydrate diphosphates, dithiodi phosphates, triphosphates, and trithiotriphosphates with high regioselectivity.

  DOI：

  10.1021/ol0521432

文献信息

• Selective Diphosphorylation, Dithiodiphosphorylation, Triphosphorylation, and Trithiotriphosphorylation of Unprotected Carbohydrates and Nucleosides
  作者：Yousef Ahmadibeni、Keykavous Parang

  DOI：10.1021/ol0521432

  日期：2005.12.1

  [GRAPHIC]Aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with diphosphitylarting and triphosphitylating reagents to yield the corresponding polymer-bound cliphosphitylating and triphosphitylating reagents, respectively. A number of unprotected carbohydrates and nucleosides were reacted with the polymer-bound reagents. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by removal of cyanoethoxy group with DBU and the acidic cleavage, respectively, afforded only one type of monosubstituted nucleoside and carbohydrate diphosphates, dithiodi phosphates, triphosphates, and trithiotriphosphates with high regioselectivity.