2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose | 120312-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose
• 英文别名: tert-Butyldimethylsilyl-2-azido-3-O-benzyl-2-desoxy-β-D-glucopyranosid；tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside；tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside；(2R,3S,4R,5R,6S)-5-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-4-phenylmethoxyoxan-3-ol
• CAS: 120312-08-5
• 化学式: C₁₉H₃₁N₃O₅Si
• 分子量: 409.558
• InChiKey: VDOMNOFUFXHLPC-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 四丁基溴化铵 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 67.75h， 生成 (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)
  参考文献：
  名称：

  Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

  摘要：

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

  DOI：

  10.1021/jo00008a040
• 作为产物：
  描述：

  2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯 在 咪唑 、 甲醇 、 4 A molecular sieve 、 氨 、 sodium methylate 、 对甲苯磺酸 、 三氟乙酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  肝素寡糖的模块化合成。

  摘要：

  描述了用于确定的肝素寡糖的首次完全立体选择性合成的通用模块化策略。利用六种单糖结构单元（四种差异保护的葡糖胺，一种葡萄糖醛酸和一种艾杜糖醛酸）以完全选择性的方式制备二糖和三糖模块。通过将构象约束置于糖醛酸糖基受体上来控制α-氨基葡萄糖连接的安装，从而建立了立体化学控制的新概念。借助C2参与基团，完全可以选择性地形成二糖模块以形成反糖醛酸键。二糖模块之间的偶联反应表现出序列依赖性。虽然许多葡糖胺糖醛酸二糖模块的结合没有遇到任何问题，某些序列证明无法访问。通过添加一个或多个葡糖胺或糖醛酸将葡糖胺糖醛酸二糖结构单元精细化为三糖模块，如类似于ATIII结合序列的六糖实例所示，该寡糖可立体选择性地进入寡糖。最终脱保护和硫酸化得到完全合成的肝素寡糖。

  DOI：

  10.1002/chem.200390009

文献信息

• Solid- and solution-phase synthesis of heparin and other glycosaminoglycans
  申请人：——

  公开号：US20030013862A1

  公开（公告）日：2003-01-16

  Described is a modular, general synthetic strategy for the preparation in solution and on a solid support of heparin, heparin-like glycosaminoglycans, glycosaminoglycans and non-natural analogs of each of them. Additionally, the modular strategy provides the basis for the preparation of combinatorial libraries and parallel libraries of defined glycosaminoglycan oligosaccharides. The defined glycosaminoglycan structures may be used in high-throughput screening experiments to identify carbohydrate sequences that regulate a host of recognition and signal-transduction processes. The determination of specific sequences involved in receptor binding holds great promise for the development of molecular tools which will allow modulation of processes underlying viral entry, angiogenesis, kidney diseases and diseases of the central nervous system. Notably, the present invention enables the automated synthesis of glycosaminoglycans in much the same fashion that peptides and oligonucleotides are currently assembled.

  描述了一种模块化的通用合成策略，用于在溶液中和固体支撑上制备肝素、类肝素糖胺聚糖、糖胺聚糖以及它们的每一种非天然类似物。此外，该模块化策略为定义的糖胺聚糖寡糖的组合库和平行库的制备提供了基础。定义的糖胺聚糖结构可以用于高通量筛选实验，以识别调节多种识别和信号转导过程的碳水化合物序列。确定参与受体结合的特定序列对于开发分子工具具有巨大的前景，这些工具将允许调节病毒进入、血管生成、肾脏疾病和中枢神经系统疾病等过程。值得注意的是，本发明使得能够以目前组装肽和寡核苷酸的方式自动化合成糖胺聚糖。
• Synthesis of Kdo-α-glycosides of lipid A derivatives
  作者：Hansjör Rembold、Richard R. Schmidt

  DOI：10.1016/0008-6215(93)84029-6

  日期：1993.8

  The synthesis of the lipopolysaccharide fragment O-(4,5,7,8-tetra-O-acetyl-3-deoxy-N-methyl-alpha-D-manno-2- octulopyranosylonamide)-(2-->6)-O-(2-deoxy-2-[(3R)-3- dodecanoyloxytetradecanamido]-4-O- phosphono-3-O-tetradecanoyl-beta-D-glucopyranosyl)-(1-->6)-1-O-acetyl-2- deoxy-2 - [(3R)-3-dodecanoyloxytetradecanamido]-3-O-tetradecanoyl-alpha-D- glucopyranose (35 alpha) is performed via anomeric O-alkylation

  脂多糖片段O-（4,5,7,8-四-O-乙酰基-3-脱氧-N-甲基-α-D-甘露糖-2-辛基吡喃酰胺）-（2-> 6）-的合成O-（2-脱氧-2-[（（3R）-3-十二烷酰氧基十四烷酰胺基] -4-O-膦酰基-3-O-十四烷酰-β-D-吡喃葡萄糖基）-（1-> 6）-1-O-经由异头O-烷基化进行乙酰基-2-脱氧-2-[（3R）-3-十二烷酰氧基四癸酰胺基] -3-O-十四烷酰基-α-D-吡喃葡萄糖（35α）。为此目的，由D-葡糖醛合成了2-叠氮基-3-O-苄基-2-脱氧-6-O-三氟甲磺酰基-β-D-glucopyranosides5、7和19 alpha，beta并用于烷基化代理商。5与O-环己叉基保护的Kdo衍生物10反应得到所需的α-连接的二糖，叔丁基二甲基甲硅烷基4-O-烯丙基-2-叠氮基3-O-苄基-2-脱氧-6-O-（ 4,5：7，8-二-O-环己叉基-3-脱氧-N-甲基-α
• Total syntheses of bulgecinine and bulgecin C from (2S,4R)-hydroxyproline
  作者：Anthony G. M. Barrett、Daniel Pilipauskas

  DOI：10.1021/jo00305a007

  日期：1990.8
• Toward the Solid-Phase Synthesis of Heparan Sulfate Oligosaccharides: Evaluation of Iduronic Acid and Idose Building Blocks
  作者：Nerea Guedes、Pawel Czechura、Begoña Echeverria、Ada Ruiz、Olatz Michelena、Manuel Martin-Lomas、Niels-Christian Reichardt

  DOI：10.1021/jo400467g

  日期：2013.7.19

  Glycan arrays have been established as the premier technical platform for assessing the specificity of carbohydrate binding proteins, an important step in functional glycomics research. Access to large libraries of well-characterized oligosaccharides remains a major bottleneck of glycan array research, and this is particularly true for glycosaminoglycans (GAGs), a class of linear sulfated polysaccharides which are present on most animal cells. Solid-supported synthesis is a potentially powerful tool for the accelerated synthesis of relevant GAG libraries with variations in glycan sequence and sulfation pattern. We have evaluated a series of iduronic acid and idose donors, including a couple of novel n-pentenyl orthoester donors in the sequential assembly of heparan sulfate precursors from monosaccharide building blocks in solution and on a polystyrene resin. The systematic study of donor and acceptor performance up to the trisaccharide stage in solution and on the solid support have resulted in a general strategy for the solid-phase assembly of this important class of glycans.
• Termin, Andreas; Schmidt, Richard R., Liebigs Annalen der Chemie, 1989, p. 789 - 796
  作者：Termin, Andreas、Schmidt, Richard R.

  DOI：——

  日期：——