phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside | 173314-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4-diacetyloxy-5-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 173314-28-8
• 化学式: C₂₅H₂₈O₈S
• 分子量: 488.559
• InChiKey: YCDPSTLKQXXGOK-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside 在 palladium on activated charcoal 1-己烯 、 4 A molecular sieve 、 氢气 、 溴 、 silver perchlorate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 silver carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 23.0 ℃ 、2.07 MPa 条件下， 反应 86.41h， 生成 methyl 6-[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[(2R,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-hydroxyoxan-2-yl]oxyoxan-2-yl]oxyhexanoate
  参考文献：
  名称：

  Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis

  摘要：

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

  DOI：

  10.1021/jo962300y
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranoside 、 苯基硫三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 以90%的产率得到phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  结核分枝杆菌多糖II的五糖片段的合成

  摘要：

  描述了立体控制的，逐步合成的α-（1→2）连接的二糖至五糖苷（1-5）的癸基糖苷；这些构成结核分枝杆菌多糖II的片段。苯基3,4,6-三-O-乙酰基-2-O-苄基-1-硫代-α-D-吡喃葡萄糖苷（7）被用作由1,3,4,6-tetra得到的单键中间体-O-乙酰基-2-O-苄基-β-D-吡喃葡萄糖（6）和PhSSiMe3。7的卤代分解得到分离的β溴化物（10）和β氯化物（13）。在没有重金属盐的情况下，用癸醇将10溶剂化，以高立体选择性反应以高收率得到癸基3,4,6-三-O-乙酰基-2-O-苄基-α-D-吡喃葡萄糖苷（14）。随后的，

  DOI：

  10.1016/0008-6215(95)00199-4

文献信息

• [EN] HEPARANASE INHIBITORS AND THEIR USE AS ANTI-CANCER COMPOUNDS<br/>[FR] INHIBITEURS D'HÉPARANASE ET LEUR UTILISATION COMME COMPOSÉS ANTICANCÉREUX
  申请人：UNIV WAYNE STATE

  公开号：WO2020118103A1

  公开（公告）日：2020-06-11

  Anti-heparanase compounds for the treatment of cancer are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also provided.

  描述了用于治疗癌症的抗肝素酶化合物。这些抗肝素酶化合物是高亲和力的合成糖聚合物，导致最小的抗凝活性。此外还提供了这些化合物的立体选择性氟化形式。
• HEPARANASE INHIBITORS FOR TREATMENT OF DIABETES
  申请人：Wayne State University

  公开号：US20210205350A1

  公开（公告）日：2021-07-08

  Anti-heparanase compounds for the treatment of diabetes are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also provided.

  描述了用于治疗糖尿病的抗肝素酶化合物。这些抗肝素酶化合物是高亲和力的合成糖聚合物，几乎不具有抗凝血活性。此外，还提供了这些化合物的立体选择性氟化形式。
• Phenanthroline‐Catalyzed Stereoretentive Glycosylations
  作者：Fei Yu、Jiayi Li、Paul M. DeMent、Yi‐Jung Tu、H. Bernhard Schlegel、Hien M. Nguyen

  DOI：10.1002/anie.201901346

  日期：2019.5.20

  limitations in synthetic access to well-defined oligosaccharides. Most of the current methods rely on the design of specialized coupling partners to control selectivity during the formation of glycosidic bonds. Reported herein is the use of a commercially available phenanthroline to catalyze stereoretentive glycosylation with glycosyl bromides. The method provides efficient access to α-1,2-cis glycosides. This

  碳水化合物是自然界中许多生物活性分子的基本组成部分。然而，阐明其作用方式的努力往往受到合成获得明确寡糖的限制的阻碍。大多数当前方法依赖于设计专门的偶联配偶体来控制糖苷键形成过程中的选择性。本文报道了使用可商购的菲咯啉来催化与糖基溴的立体保留糖基化。该方法提供了对 α-1,2-cis 糖苷的有效获取。该协议已用于八糖佐剂的大规模合成。密度泛函理论计算以及动力学研究表明，该反应通过双 SN 2 机制进行。