(1R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2-oxa-bicyclo[4.1.0]heptane | 162428-32-2

• 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: (1R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2-oxa-bicyclo[4.1.0]heptane
• 英文别名: (1R,3R,4R,5R,6S)-4,5-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane
• CAS: 162428-32-2
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: KNARNYHTGSHJAX-PKLSKMGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2-oxa-bicyclo[4.1.0]heptane 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以82%的产率得到3,4,6-tri-O-benzyl-2-deoxy-2-methylene-D-lyxo-hexono-1,5-lactone
  参考文献：
  名称：

  A Facile Synthesis of Chiral α-Methylene-δ-Valerolactones

  摘要：

  手性α-亚甲基-β-戊内酯是通过一锅中的 1,2-环丙烷糖与二(s-可力丁)高氯酸碘 (IDCP) 反应获得的。

  DOI：

  10.1055/s-1997-5764
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 lithium aluminium tetrahydride 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.5h， 生成 (1R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2-oxa-bicyclo[4.1.0]heptane
  参考文献：
  名称：

  [EN] IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS
  [FR] ASSEMBLAGE IN VIVO D'AGENTS THÉRAPEUTIQUES DE LIAISON À ASGPR

  摘要：

  公开号：

  WO2022035997A9

文献信息

• Platinum-Catalyzed Ring Opening of 1,2-Cyclopropanated Sugars with <i>O</i>-Nucleophiles. Convenient Synthesis of 2-<i>C</i>-Branched Carbohydrates
  作者：Jürgen Beyer、Philip R. Skaanderup、Robert Madsen

  DOI：10.1021/ja001558+

  日期：2000.10.1

  in the ring opening with alcohols regardless of the stereochemistry of the starting cyclopropane. When electron-rich phenols are employed as O-nucleophiles, rearrangement to the glycosyl arene has been observed. In general, the ring opening occurs readily with unsubstituted sugar cyclopropanes to give 2-C-methyl carbohydrates. However, cyclopropanes with ester or alkyl substituents are significantly

  描述了一种由 Zeise 的二聚体催化的新反应，该反应允许 1,2-环丙烷化糖与 O-亲核试剂开环，得到 2-C-支链碳水化合物。许多 O-亲核试剂可以参与开环，包括醇类、酚类和水。已使用范围广泛的醇，产生从简单的甲基糖苷到更复杂的二糖的 2-C 支链糖苷。在新形成的 C-1 立体中心获得了非常高的非对映选择性。无论起始环丙烷的立体化学如何，α-糖苷受异头效应的青睐，始终是与醇开环的主要产物。当富电子酚用作 O-亲核试剂时，已观察到重排为糖基芳烃。一般来说，未取代的糖环丙烷很容易开环，得到 2-C-甲基碳水化合物。然而，带有酯或烷基取代基的环丙烷反应性明显较低，有些甚至完全在...
• [EN] ASGPR-BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS<br/>[FR] COMPOSÉS SE LIANT À L'ASGPR POUR LA DÉGRADATION DE PROTÉINES EXTRACELLULAIRES
  申请人：AVILAR THERAPEUTICS INC

  公开号：WO2021155317A1

  公开（公告）日：2021-08-05

  Compounds and compositions that have an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein are described.

  描述了将一个与外细胞蛋白结合配体结合的阿斯利康糖蛋白受体（ASGPR）结合配体的化合物和组合物，用于选择性降解体内靶外细胞蛋白以治疗由外细胞蛋白介导的疾病。
• Synthesis of 1,2-cyclopropanated sugars from glycals
  作者：R. Murali、C. V. Ramana、M. Nagarajan

  DOI：10.1039/c39950000217

  日期：——

  Syntheses of both forms of cyclopropanated sugars from glycals by (i) Simmons–Smith reaction and (ii) dichiorocarbene addition followed by dehalogenation are described.

  描述了通过(i) Simmons–Smith反应和(ii) 二氯甲烯添加后去卤化的方法合成两种形式的环丙烷糖。
• Novel Platinum-Catalyzed Ring-Opening of 1,2-Cyclopropanated Sugars with Alcohols. Stereoselective Synthesis of 2-C-Branched Glycosides
  作者：Jürgen Beyer、Robert Madsen

  DOI：10.1021/ja982964k

  日期：1998.11.1
• Synthesis and Reactions of 1,2-Cyclopropanated Sugars
  作者：C. V. Ramana、R. Murali、M. Nagarajan

  DOI：10.1021/jo970948k

  日期：1997.10.1

  Diastereospecific cyclopropanation of glycals 1, 2, 3, 4, and 41 was carried out using either dihalocarbene addition or zinc-carbenoid addition to yield 1,2-cyclopropanated sugars. Dichloro- and dibromocarbenes added stereoselectively anti to the C-3 benzyloxy group, whereas (under Simmons-Smith conditions) the cyclopropanes were formed syn to the same substituent. The reactions of these 1,2-cyclopropanated sugars to provide either ring expanded glycosides or C-2-branched chain glycosides were explored. Solvolytic ring expansion of 1,2-dibromocyclopropanated sugars with K2CO3 in refluxing methanol yielded the corresponding chiral oxepins 20-22. Electrophilic ring openings of parent cyclopropanes (14 and 17 derived from glucal 1) were carried out with different electrophiles to give functionalized 2-deoxy-2-C-branched chain glycosides. The ring openings of 14 in different solvents resulted in both alpha- and beta-anomers, whereas 17 gave exclusively the alpha-anomer.