dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate | 604767-71-7

• 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: dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate
• 英文别名: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate；di-n-butylphosphoryl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside；[(2S,3R,4S,5R,6R)-2-dibutoxyphosphoryloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 604767-71-7
• 化学式: C₃₇H₄₉O₁₀P
• 分子量: 684.764
• InChiKey: OEEWGCNSDJHSRW-MANRWTMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  48
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  C₁₀₄H₁₁₁N₃O₂₀ 、 dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 C₁₃₃H₁₄₁N₃O₂₆
  参考文献：
  名称：

  [EN] SYNTHETIC OLIGOSACCHARIDES FOR MORAXELLA VACCINE
  [FR] OLIGOSACCHARIDES SYNTHÉTIQUES POUR VACCINS CONTRE MORAXELLA

  摘要：

  公开号：

  WO2011137181A8
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranoside 、 磷酸二丁酯 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate
  参考文献：
  名称：

  Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions

  摘要：

  A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.

  DOI：

  10.1021/ol0603155

文献信息

• Methyltrioxorhenium catalyzed domino epoxidation-nucleophilic ring opening of glycals
  作者：Gianluca Soldaini、Francesca Cardona、Andrea Goti

  DOI：10.1016/s0040-4039(03)01386-8

  日期：2003.7

  The use of catalytic methylrhenium trioxide (MTO) and urea hydrogen peroxide in room temperature ionic liquid for the hydroxyglycosylation with glycals in a domino fashion is reported. Excellent conversions and good selectivities for the epoxidation reaction were observed. Application to the synthesis of glycosylphosphates, good glycosyl donors, has been studied. (C) 2003 Elsevier Ltd. All rights reserved.
• Catalytic Oxidation−Phosphorylation of Glycals:  Rate Acceleration and Enhancement of Selectivity with Added Nitrogen Ligands in Common Organic Solvents
  作者：Gianluca Soldaini、Francesca Cardona、Andrea Goti

  DOI：10.1021/ol047417k

  日期：2005.2.1

  [GRAPHICS]The first general catalytic oxidation of glycals has been developed to afford useful glycosyl phosphates in high yield and selectivity in a domino process with the use of catalytic methyltrioxorhenium, urea hydrogen peroxide, stoichiometric dibutyl phosphate as nucleophile, and a substoichiometric amount of nitrogen ligands, such as pyridine or imidazole, in organic solvents.