(2β,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol | 77737-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2β,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol
• 英文别名: (2S,3S,4R,5S,6R)-2-ethenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 77737-59-8
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: UFXIZCQEFAYYDJ-UCWKTGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2β,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以75%的产率得到(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxiranyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Synthesis of trans-fused perhydrofuropyrans and related α-methylene lactones: bicyclic ring-systems present in the ezomycins, the octosyl acids, and certain antitumor terpenoids

  摘要：

  DOI：

  10.1016/s0008-6215(00)84618-2
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-1,2-O-(isopropoxyethylidene)-α-D-glucopyranoside 在 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 (2β,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  Synthesis of trans-fused perhydrofuropyrans and related α-methylene lactones: bicyclic ring-systems present in the ezomycins, the octosyl acids, and certain antitumor terpenoids

  摘要：

  DOI：

  10.1016/s0008-6215(00)84618-2

文献信息

• Synthesis of Hybrids of D-Glucose and D-Galactose with Pyrrolidine-Based Iminosugars as Glycosidase Inhibitors
  作者：Venkata Ramana Doddi、Hari Prasad Kokatla、A. P. John Pal、Ranjan K. Basak、Yashwant D. Vankar

  DOI：10.1002/ejoc.200800770

  日期：2008.12

  Sugar-iminosugar hybrid molecules made up of D-glucose and D-galactose with pyrrolidine-based iminosugars, viz. 1,4-dideoxy-1,4-imino-L-xylitol and 1,4-dideoxy-1,4-imino-L-lyxitol, are synthesized from glycal epoxides and found to be moderate glycosidase inhibitors.

  由 D-葡萄糖和 D-半乳糖与基于吡咯烷的亚氨基糖组成的糖-亚氨基糖杂化分子，即。1,4-dideoxy-1,4-imino-L-xylitol 和 1,4-dideoxy-1,4-imino-L-lyxitol 是由糖基环氧化物合成的，是中度糖苷酶抑制剂。
• A Cascade “Prins-Pinacol-Type Rearrangement and C4-OBn Participation” on Carbohydrate Substrates: Synthesis of Bridged Tricyclic Ketals, Annulated Sugars and C2-Branched Heptoses
  作者：Parasuraman Rajasekaran、Govind Pratap Singh、Mohammad Hassam、Yashwant D. Vankar

  DOI：10.1002/chem.201604902

  日期：2016.12.19

  pinacol type rearrangement followed by C4‐OBn participation” in a cascade manner has been observed while probing the fate of carbocation in some carbohydrate derived homoallylic alcohols in the Prins reaction. This has led to an easy access to tetrahydrofuran‐fused bridged bicyclic ketals (or tetrahydrofuran‐fused 1,6‐anhydro‐heptopyranose frameworks) which are further converted into some annulated sugars

  在探查Prins反应中某些碳水化合物衍生的均丙醇中碳正离子的去向时，已观察到以级联方式发生的“ Prins频哪醇类型重排，然后C4-OBn参与”。这使得容易获得四氢呋喃融合的桥联双环缩酮（或四氢呋喃融合的1,6-脱水-庚基吡喃糖骨架），然后将其进一步转化为一些环状糖和C2支化的庚糖。
• Highly stereoselective synthesis of C-vinyl pyranosides via a Pd0-mediated cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enitols
  作者：Ernest G. Nolen、Vivian C. Ezeh、Matthew J. Feeney

  DOI：10.1016/j.carres.2014.07.002

  日期：2014.9

  Oct-2-enitols undergo a Pd(0)-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical preference during cyclization, the α- and β-epimeric ratios are enhanced by double diastereoselection using the (S,S) or (R,R)-DACH ligands.
• Synthesis of trans-fused perhydrofuropyrans and related α-methylene lactones: bicyclic ring-systems present in the ezomycins, the octosyl acids, and certain antitumor terpenoids
  作者：Stephen Hanessian、Teng Jiam Liak、Dilip M. Dixit

  DOI：10.1016/s0008-6215(00)84618-2

  日期：1981.1