1-thio-α-fucopyranose | 736100-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-thio-α-fucopyranose
• 英文别名: (2S,3S,4R,5S,6S)-2-methyl-6-sulfanyloxane-3,4,5-triol
• CAS: 736100-60-0
• 化学式: C₆H₁₂O₄S
• 分子量: 180.225
• InChiKey: SGCGFOOGTWZYCQ-KGJVWPDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.9
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-thio-α-fucopyranose 生成 1-thio-β-L-fucopyranose
  参考文献：
  名称：

  pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-d-Aldopyranoses

  摘要：

  The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the beta-anomer at lower pH to the alpha-anomer at higher pH.

  DOI：

  10.1021/jo100826e
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 生成 1-thio-α-fucopyranose
  参考文献：
  名称：

  S-Neofucopeptides 作为 E-和 P-选择素抑制剂的合成和生物学评价

  摘要：

  显示了 α/β-L-岩藻糖基化半胱胺、3-硫代丙酸和 3-硫代乙酸衍生物作为制备 S-新岩藻糖肽的构建块的合成。这些化合物用于合成新的硫代岩藻糖苷衍生物（8α、9α、9β、10α、22α、22β、24α、26α），这些衍生物对 E-和 P-选择蛋白具有亲和力。它们构成了天然 SLex 四糖的一系列新的水解稳定和低分子量模拟物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800199

文献信息

• [EN] MANNOSE PHOSPHATE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION<br/>[FR] DÉRIVÉS DE MANNOSE PHOSPHATE EN TANT QU'ANTAGONISTES DE L'ADHÉSION BACTÉRIENNE
  申请人：UNIV BASEL

  公开号：WO2012164074A1

  公开（公告）日：2012-12-06

  Compounds of the formula (I) (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are, independent of each other, hydrogen or a substituent as described in the specification, and one of RA, RB, RC and RD is P02(OH)2 and the other ones are hydrogen; are orally available medicaments useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.

  公式(I)（I）化合物，其中n为0、1或2，R1为芳基、杂芳基或杂环基，R2和R3独立地为氢或如说明书中所描述的取代基，且RA、RB、RC和RD中的一个为P02(OH)2，其余为氢；是口服可用的药物，用于预防和治疗细菌感染，特别是由大肠杆菌引起的尿路感染。
• MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION
  申请人：Ernst Beat

  公开号：US20120270824A1

  公开（公告）日：2012-10-25

  Compounds of the formula (I) wherein n is 0, 1 or 2, R 1 is aryl, heteroaryl or heterocyclyl, and R 2 and R 3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli .

  式(I)的化合物，其中n为0、1或2，R1为芳基、杂芳基或杂环基，R2和R3为氢或规范中所述的取代基，对于预防和治疗细菌感染，特别是由大肠杆菌引起的尿路感染是有用的。
• Mannose derivatives as antagonists of bacterial adhesion
  申请人：University of Basel

  公开号：EP2604619A2

  公开（公告）日：2013-06-19

  Compounds of the formula (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.

  式 (I) 的化合物 其中 n 为 0、1 或 2，R1 为芳基、杂芳基或杂环基，R2 和 R3 为氢或说明书中所述的取代基，可用于预防和治疗细菌感染，特别是由大肠杆菌引起的泌尿系统感染。
• PHENYL-ALPHA-D-MANNOSIDES FOR USE IN THE TREATMENT OF BACTERIAL INFECTIONS CAUSED BY ESCHERICHIA COLI
  申请人：University of Basel

  公开号：EP2960247A1

  公开（公告）日：2015-12-30

  Compounds of the formula (I) wherein n is 0, 1 or 2, R2 and R3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli, wherein R1 is one of groups (B), (C), (D), (E) below:

  式（I）化合物，其中 n 为 0、1 或 2，R2 和 R3 为氢或说明书中所述的取代基，可用于预防和治疗细菌感染，特别是由大肠杆菌引起的泌尿系统感染、 其中 R1 为以下 (B)、(C)、(D)、(E) 组之一：
• Electrochemical nickel-catalyzed cross-coupling of glycosyl thiols with preactivated phenols and ketones
  作者：Fuxin Li、Hui Liu、Wanyu Xing、Qingju Zhang、Liming Wang

  DOI：10.1039/d4ob00442f

  日期：——

  An efficient electrochemical nickel-catalyzed cross-coupling reaction has been reported here for the synthesis of S-glycosides from preactivated phenols and ketones under mild conditions. Various glycosyl thiols, including unprotected sugar, and a diverse range of aryl/alkenyl triflates, including some complex biorelevant phenols and ketones, were well tolerated in this method.

  本文报道了一种有效的电化学镍催化交叉偶联反应，用于在温和条件下从预活化的酚和酮合成S-糖苷。该方法对各种糖基硫醇（包括未保护的糖）和各种芳基/烯基三氟甲磺酸酯（包括一些复杂的生物相关酚和酮）具有良好的耐受性。