ethyl 2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-1-thio-β-D-mannopyranoside | 199116-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-1-thio-β-D-mannopyranoside
• 英文别名: ethyl 3,4,6-tri-O-benzyl-2-O-(tert-butyldimethylsilyl)-1-thio-β-D-mannopyranoside；2-tert-butyldimethylsilyl 3,4,6-tribenzyl-1-thioethyl D-mannoside
• CAS: 199116-17-1
• 化学式: C₃₅H₄₈O₅SSi
• 分子量: 608.915
• InChiKey: DSKTXNGTVWZMTI-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-O-p-methoxybenzyl-D-glucal 、 ethyl 2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-1-thio-β-D-mannopyranoside 在 二叔丁基过氧化物 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到
  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
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 sodium tetrahydroborate 、 乙酸酐 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 ethyl 2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

  摘要：

  The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15 -> 18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34 -> 36). Another key strategic element involved the epimerization of an interior core glucoside to reach the P-mannoside (see 37 -> 38) required in the ring C sugar of the high mannose core. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.080

文献信息

• Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins
  作者：Mirella Wawryszyn、Paul F. Sauter、Martin Nieger、Martin R. M. Koos、Christine Koehler、Burkhard Luy、Edward A. Lemke、Stefan Bräse

  DOI：10.1002/ejoc.201800602

  日期：2018.8.23

  An azido‐glycan core structure was modified into the protected N‐glycan pentasaccharide core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins.

  叠氮基聚糖核心结构被修改为受保护的N聚糖五糖核心结构。叠氮基功能允许与具有非典型环辛炔氨基酸的重组修饰蛋白进行化学连接，从而获得糖蛋白的定制糖模式。