(2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran

• 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: (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran
• 英文别名: (2S,3R,4S,5S,6R)-2-bromo-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₃₄H₃₅BrO₅
• 分子量: 603.553
• InChiKey: WXYNLXPSTFTJJC-BWNLSPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 1.0h， 生成 N-acetyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Large Scale Synthesis of A Derivative of An α-Galactosyl Trisaccharide Epitope Involved in the Hyperacute Rejection of Xenotransplantation

  摘要：

  A derivative of an alpha-galactosyl trisaccharide xenoactive antigen, (2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1-->3)-(2,4,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide (5), was synthesized on a large scale (50 gram). The synthesis involved a high yielding and highly stereoselective (alpha \beta>20:1) glycosylation reaction utilizing a thiogalactoside as the donor and a selectively protected lactose azide as the acceptor. This derivative serves as a versatile intermediate that can be transformed into a variety of alpha-Gal containing glycoconjugates highly desired in xenotransplantation research and pharmaceutical development.

  DOI：

  10.1080/07328309908544050
• 作为产物：
  描述：

  乙基-2,3,4,6-O-四苄基-Beta-D-硫代半乳糖苷 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran
  参考文献：
  名称：

  4-戊烯基糖苷在合成与肺炎克雷伯菌的半乳聚糖 I 相关的四糖中的吡喃糖苷到呋喃糖苷的重排

  摘要：

  据报道，一种合成与肺炎克雷伯菌半乳聚糖 I 相关的间隔臂四糖的有效策略采用新开发的无酸条件，用于在异头位置带有 4-戊烯基的双半乳糖苷的吡喃糖苷转化为呋喃糖苷 (PIF) 重排。4-戊烯基苷元成功地用作 3-三氟乙酰氨基丙醇糖基化中的离去基团，并作为临时异头保护，使其转化为亚胺酸酯供体。二糖块的区域选择性偶联提供了研究半乳聚糖 I 与免疫系统蛋白质相互作用所需的所需四糖序列。

  DOI：

  10.1002/ejoc.201601413

文献信息

• Glycomimetic inhibitors of the PA-IL lectin, PA-IIL lectin or both the lectins from pseudomonas
  申请人：Magnani L. John

  公开号：US20070037775A1

  公开（公告）日：2007-02-15

  Compositions and methods are provided related to Pseudomonas bacteria. The compositions and methods may be used for diagnosis and therapy of medical conditions involving infection with Pseudomonas bacteria. Such infections include Pseudomonas aeruginosa in the lungs of patients with cystic fibrosis. A compound useful in the present methods may be used in combination with a therapeutic agent or may be linked to a therapeutic agent. Pseudomonas bacteria may be inhibited by blocking colonization, inhibiting virulence factors, arresting growth or killing the bacteria.

  提供与铜绿假单胞菌相关的组合物和方法。这些组合物和方法可用于诊断和治疗涉及铜绿假单胞菌感染的医疗状况。这些感染包括囊性纤维化患者肺部中的铜绿假单胞菌。在目前的方法中有用的化合物可以与治疗剂结合使用，或者可以与治疗剂连接。通过阻止定植、抑制毒力因子、阻止生长或杀死细菌可以抑制铜绿假单胞菌。
• Process for the production of peracylated 1-0-glycosides
  申请人：Schering AG

  公开号：US20030069402A1

  公开（公告）日：2003-04-10

  The invention relates to a process for the production of peracylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar is a monosaccharide that is functionalized in 1-OH-position, R represents methyl, ethyl, propyl, isopropyl, tbutyl, phenyl, n means 2, 3 or 4, X means —COO— or —NH—and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of peracylated saccharides with 1-O-functionalized side chains on an enlarged scale.

  该发明涉及一种生产通式I的过酰化1-O-糖苷或其盐的工艺，其中糖是在1-OH位置上被官能化的单糖，R代表甲基、乙基、丙基、异丙基、叔丁基、苯基，n取2、3或4，X代表—COO—或—NH—，L代表一条直链、分支、饱和或不饱和的C1-C30碳链，该碳链可以被基团中断或取代。根据该发明的工艺从经济实惠的起始材料开始，提供良好的产量，并允许在扩大规模上生产具有1-O官能化侧链的过酰化糖苷。
• Process for the production of perbenzylated 1-O-glycosides
  申请人：——

  公开号：US20030055242A1

  公开（公告）日：2003-03-20

  The invention relates to a process for the production of perbenzylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar 1 is a monosaccharide that is functionalized in 1-OH-position, R represents benzyl, n means 2, 3 or 4, X means —COO— or —NH— and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of perbenzylated saccharides with 1-O-functionalized side chains on an industrial scale.

  该发明涉及一种生产通式I的过苄基化1-O-糖苷或其盐的方法，其中糖1是在1-OH位置上官能化的单糖，R代表苄基，n为2、3或4，X代表—COO—或—NH—，L代表直链、支链、饱和或不饱和的C1-C30碳链，该碳链可以选择性地被基团中断或取代。根据该发明的方法从经济起始材料开始，提供良好的产率，并允许在工业规模上生产具有1-O官能化侧链的过苄基化糖类。
• Process for the production of perbenzylated 1-0-glycosides
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：US20020002274A1

  公开（公告）日：2002-01-03

  The invention relates to a process for the production of perbenzylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar 1 is a monosaccharide that is functionalized in 1 -OH-position, R represents benzyl, n means 2, 3 or 4, means —O—, —S—, —COO— or —NH— and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of perbenzylated saccharides with 1-O-functionalized side chains on an enlarged scale.

  本发明涉及一种生产通式I的1-O-苄基化糖苷或其盐的过程，其中糖1是在1-OH位置上官能化的单糖，R代表苄基，n为2、3或4，代表-O、S、COO或NH，L代表直链、支链、饱和或不饱和的C1-C30碳链，该碳链可以被中断或取代。本发明的过程从经济实惠的起始材料开始，提供良好的产量，并允许在扩大规模上生产1-O官能化侧链的苄基化糖苷。
• [EN] GLYCOMIMETIC INHIBITORS OF PA-IL AND PA-IIL LECTINS<br/>[FR] INHIBITEURS GLYCOMIMÉTIQUES DES LECTINES PA-IL ET PA-IIL
  申请人：GLYCOMIMETICS INC

  公开号：WO2017127422A1

  公开（公告）日：2017-07-27

  Compounds, compositions, and methods for the diagnosis and/or treaimeni of medical conditions involving infections with and colonization by Fseudomonas bacteria including, for example, Fseudomonas aeruginosa in the lungs of patients with cystic fibrosis are described.

  描述了涉及感染和定植由铜绿假单胞菌引起的医疗状况的诊断和/或治疗的化合物、组合物和方法，例如囊性纤维化患者肺部中的铜绿假单胞菌。