(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol | 15548-45-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• 英文别名: benzyl α-D-mannopyranoside；Benzyl-α-D-mannopyranosid；benzyl α-D-mannoside；benzyl α-mannopyranoside；Benzyl alpha-D-mannopyranoside；(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4,5-triol
• CAS: 15548-45-5
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: GKHCBYYBLTXYEV-BNDIWNMDSA-N

物化性质

• 熔点：
  126-129°C
• 沸点：
  480.2±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 在 钯 吡啶 、 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 3 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 重水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 243.0h， 生成 八倾吲嗪三醇
  参考文献：
  名称：

  Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose

  摘要：

  DOI：

  10.1016/s0040-4020(01)86850-2
• 作为产物：
  描述：

  benzyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 以91%的产率得到(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
  参考文献：
  名称：

  FimH Antagonists for the Oral Treatment of Urinary Tract Infections: From Design and Synthesis to in Vitro and in Vivo Evaluation

  摘要：

  Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pill, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of alpha-D-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.

  DOI：

  10.1021/jm101011y

文献信息

• Preparation of Thiosugars and Their Use
  申请人：Davis Benjamin Guy

  公开号：US20090176970A1

  公开（公告）日：2009-07-09

  A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

  一种制备由糖硫代糖（Saccharide-S-H）表示的硫代糖的方法，其中糖代表至少4个糖单元，包括将具有以下结构的相应化合物（P）糖硫代糖（P）进行桦还原：（P）糖硫代糖（P），其中（P）代表一个或多个O-或S-保护基。
• Convenient Synthesis of 4,6-<i>O</i>-Pyruvate Acetal Containing Glycosides via Tetraisopropyldisiloxanediyl Protected Sugars
  作者：Thomas Ziegler、Elisabeth Eckhardt、Karin Neumann、Veronique Birault

  DOI：10.1055/s-1992-26291

  日期：——

  Treatment of alkyl D-glycopyranosides and alkyl or phenyl 1-thio-ß-D-glycopyranosides 1 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gave the corresponding 4,6-O-(1,1,3,3-tetraisopro-pyldisiloxane-1,3-diyl) protected glycosides 2 which were subsequently benzoylated with benzoyl bromide to give the fully blocked glycosides 3. Reaction of the latter with methyl pyruvate and a catalytic amount of trimethylsilyl trifluoromethanesulfonate gave alkyl and phenyl 4,6-O-[1-(methoxycarbonyl)ethylidene]glycopyranosides 4 with high diastereoselectivity.

  烷基 D-吡喃葡糖苷和烷基或苯基1-硫-ß-D-吡喃葡糖苷 1 与1,3-二氯-1,1,3,3-四异丙基二硅氧烷反应，得到相应的4,6-O-(1,1,3,3-四异丙基二硅氧烷-1,3-二基)保护的糖苷 2，随后用苯甲酰溴进行苯甲酰化，得到完全保护的糖苷 3。后者与丙酮酸甲酯和少量三甲基硅基三氟甲磺酸酯反应，以高非对映选择性得到烷基和苯基4,6-O-[1-(甲氧羰基)乙叉]吡喃葡糖苷 4。
• A Simple Synthesis of Methyl 2,3,6- and 2,4,6-Tri-<i>O</i>-benzyl-α-D-mannosides
  作者：Shinkiti Koto、Kazuhiro Takenaka、Naohiko Morishima、Akiko Sugimoto、Shonosuke Zen

  DOI：10.1246/bcsj.57.3603

  日期：1984.12

  Cotrolled benzylation of methyl α-D-mannopyranoside with benzyl chloride and LiOH selectively gave the 2,3,6-tribenzyl ether in a 53% yield. Such a reaction using benzyl chloride and KOH afforded mainly the 2,4,6-tribenzyl ether in a 41% yield. The products were allylated and then hydrolyzed to give the corresponding 1-OH derivatives.

  用苄基氯和 LiOH 控制甲基 α-D-吡喃甘露糖苷的苄基化反应，选择性地得到 2,3,6-三苄基醚，产率为 53%。使用苄基氯和KOH的这种反应主要以41%的产率提供2,4,6-三苄基醚。产物被烯丙基化，然后水解得到相应的1-OH衍生物。
• Methods And Systems For Growing Plants Using Silicate-Based Substrates, Cultivation Of Enhanced Photosynthetic Productivity And Photosafening By Utilization Of Exogenous Glycopyranosides For Endogenous Glycopyranosyl-Protein Derivatives, And Formulations, Processes And Systems For The Same
  申请人：Innovation Hammer, LLC

  公开号：US20140331555A1

  公开（公告）日：2014-11-13

  Methods for promoting plant growth based on novel photosafening treatment regimes with glycopyranosides including glycopyranosylglycopyranosides, and aryl-a-D-glycopyranosides, and more specifically, with one or more compounds comprising terminal mannosyl-triose, optionally in the presence of light enhanced by one or more light reflecting and/or refracting members such as silicon-based substrates. Furthermore, chemical synthesis processes for the above compounds are disclosed for general application to plants. Silicate microbeads of the like are distributed over the ground or substrate in which roots of a plant are supported and planted, beneath and around a plant in a manner that light is refracted or reflected toward the phylloplane.

  基于新型光保护处理方案促进植物生长的方法，包括甘露聚糖苷类化合物，如甘露聚糖苷和芳基-a-D-甘露聚糖苷，更具体地，使用含有端基甘露三糖的一个或多个化合物，可选地在存在硅基基底等一个或多个反射和/或折射光的成员的情况下增强光线。此外，还公开了上述化合物的化学合成过程，以供普遍应用于植物。类似的硅酸盐微珠分布在植物的根部支撑和种植的地面或基质上，在植物的下方和周围，使光线以折射或反射的方式朝向叶面。
• Halide-mediated regioselective 6-O-glycosylation of unprotected hexopyranosides with perbenzylated glycosyl bromide donors
  作者：Dominika Alina Niedbal、Robert Madsen

  DOI：10.1016/j.tet.2015.11.059

  日期：2016.1

  couplings were completely selective for both glucose and galactose donors and acceptors as long as the stannylene acetal of the acceptor was soluble in dichloromethane. This gave rise to a number of 1,2-cis-linked disaccharides in reasonable yields. Mannose donors and acceptors, on the other hand, did not react in the glycosylation under these conditions.

  已经用二丁基氧化锡作为导向剂研究了在2,3,4,6-未保护的己吡喃糖苷中6-位的区域和立体选择性糖基化。使用全苄基化的六吡喃糖基溴化物作为供体，并且通过四丁基溴化铵促进糖基化。只要受体的亚锡乙缩醛可溶于二氯甲烷，偶联对于葡萄糖和半乳糖供体和受体都是完全选择性的。这以合理的产率产生了许多1,2-顺式连接的二糖。另一方面，在这些条件下，甘露糖供体和受体在糖基化中不反应。