(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol | 511274-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-4,5-dimethoxy-6-phenylsulfanyloxan-3-ol
• CAS: 511274-40-1
• 化学式: C₁₄H₂₀O₅S
• 分子量: 300.376
• InChiKey: NNAIXQKGZLYCCP-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol 在 四丁基碘化铵 、 镍 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.5h， 生成 (2R,3R,4R,5S)-3-Allyloxy-2-allyloxymethyl-4,5-dimethoxy-tetrahydro-pyran
  参考文献：
  名称：

  A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity

  摘要：

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

  DOI：

  10.1021/jo051021k
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-glucopyranose 在 D(+)-10-樟脑磺酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以97%的产率得到(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity

  摘要：

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

  DOI：

  10.1021/jo051021k

文献信息

• Preparation and use of carbohydrate-based ring structures with antimicrobial and cytostatic activity
  申请人：Kemin Pharma Europe

  公开号：EP2168972A2

  公开（公告）日：2010-03-31

  A compound of the formula : wherein R1 is -H, -SPh, -Ph, -allyl or -benzyl; R2 is -H, -Et, -allyl, -Me or -benzyl; R3 is -H, -Et, -Me, -allyl or -benzyl; and R4 and R5 are both -OH or R4 and R5 together form a ring and are -OCH(Ph)O- ; or a pharmaceutically active derivative thereof. Pharmaceutical compositions comprising the above compounds and their use in therapy are also provided.

  式中的化合物： 其中 R1 是-H、-SPh、-Ph、-烯丙基或-苄基； R2 是-H、-Et、-烯丙基、-Me 或-苄基 R3 是-H、-Et、-Me、-烯丙基或-苄基；以及 R4 和 R5 都是-OH，或者 R4 和 R5 共同形成一个环，并且是-OCH(Ph)O-； 或其药用活性衍生物。 还提供了包含上述化合物的药物组合物及其在治疗中的用途。
• US7534871B2
  申请人：——

  公开号：US7534871B2

  公开（公告）日：2009-05-19
• A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity
  作者：Petra Blom、Bart Ruttens、Steven Van Hoof、Idzi Hubrecht、Johan Van der Eycken、Benedikt Sas、Johan Van hemel、Jan Vandenkerckhove

  DOI：10.1021/jo051021k

  日期：2005.11.1

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.