[(2R,3S,4R,5R,6S)-5-(benzenesulfonamido)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl] acetate | 187879-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-5-(benzenesulfonamido)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl] acetate
• CAS: 187879-68-1
• 化学式: C₄₈H₅₁NO₁₁S
• 分子量: 849.999
• InChiKey: XJYXLBBLLXQVAV-LWZXJHNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  61
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-5-(benzenesulfonamido)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl] acetate 在 2,6-二甲基吡啶 、 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (2R,3S,4R,5R,6S)-5-benzenesulfonylamino-6-[(2R,3S,4R,5R,6R)-5-benzenesulfonylamino-4-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yloxy]-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  一条通往N-连接糖蛋白核心五糖的简明路线

  摘要：

  描述了N-连接糖蛋白的常见五糖核心的简明制备方法。还原末端的糖基化在壳二糖的水平上进行功能化，然后使用Crich的直接偶联方案将其进行β-甘露糖基化。分支甘露糖残基的脱保护和二α-甘露糖基化完成了合成。

  DOI：

  10.1016/s0040-4039(03)00101-1
• 作为产物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-D-glucal 在 二叔丁基过氧化物 、 iodonium(di-γ-collidine) perchlorate 、 三氟甲烷磺酸甲酯 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S,4R,5R,6S)-5-(benzenesulfonamido)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl] acetate
  参考文献：
  名称：

  A Highly Convergent Total Synthetic Route to Glycopeptides Carrying a High-Mannose Core Pentasaccharide DomainN-linked to a Natural Peptide Motif

  摘要：

  AbstractN‐Linked glycopeptides were synthesized by condensation of a highmannose anomeric amine bearing a pentasaccharide with aspartic‐acid‐containing tri‐ and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the „core”︁ region of all asparagine‐linked glycoproteins, was assembled by means of glycal‐derived thioethyl donors and glycal acceptors. The central mannose residue was established by inversion of the C2 hydroxyl of a glucosyl precursor in the pentasaccharide. The protecting‐group scheme employed allows the extension of the pentasaccharide through the terminal mannose units. While a fully convergent coupling of the high‐mannose carbohydrate to the peptide domain has thus been accomplished for the first time with a fully synthetic sugar, the stereochemical integrity of the anomeric center of the carbohydrate domain was not maintained and a mixture of glycopeptides was obtained.

  DOI：

  10.1002/chem.19970031011

文献信息

• Toward a Prostate Specific Antigen-Based Prostate Cancer Diagnostic Assay: Preparation of Keyhole Limpet Hemocyanin -Conjugated Normal and Transformed Prostate Specific Antigen Fragments
  作者：Vadim Y. Dudkin、Justin S. Miller、Anna S. Dudkina、Christophe Antczak、David A. Scheinberg、Samuel J. Danishefsky

  DOI：10.1021/ja8028137

  日期：2008.10.15

  Prostate specific antigen (PSA) molecules secreted by cancerous and normal prostate cells differ in their N-linked glycan composition, while the peptide backbone appears to be conserved. Antibodies selectively recognizing such differentially glycosylated PSA structures could form a basis for a new diagnostic assay for prostate cancer. Twenty-amino acid PSA fragments carrying di-, tri-, and tetrabranched complex-type glycans were prepared by total synthesis and conjugated to maleimide-modified keyhole limpet hemocyanin (KLH) carrier protein through backbone Cys residues. These glycopeptide/KLH conjugates were then used for antibody generation.