dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl) phosphate | 471930-57-1

• 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-galactopyranosyl) phosphate
• 英文别名: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl) phosphate；dibutyl 2-acetyl-3,4,6-tribenzyl-β-D-galactopyranosyl phosphate；[(2S,3R,4S,5S,6R)-2-dibutoxyphosphoryloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 471930-57-1
• 化学式: C₃₇H₄₉O₁₀P
• 分子量: 684.764
• InChiKey: OEEWGCNSDJHSRW-AESTUDHESA-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：

  dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl) phosphate 、 n-pentenyl 4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl-(1->3)-2,4,6-tribenzyl-α-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以88%的产率得到n-pentenyl 2-acetyl-3,4,6-tribenzyl-β-D-Galp-(1->3)-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-Galp-(1->3)-2,4,6-tribenzyl-α-D-Galp-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-Galp-(1->4)-3,6-dibenzyl-2-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+
• 作为产物：
  描述：

  磷酸二丁酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 dibutyl (2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl) phosphate
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+

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.
• Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions
  作者：Alessandra Ravidà、Xinyu Liu、Linda Kovacs、Peter H. Seeberger

  DOI：10.1021/ol0603155

  日期：2006.4.1

  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.
• 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.