(2β,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol | 440362-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2β,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol
• 英文别名: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-ol；(2S,3S,4R,5R,6R)-2-ethenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 440362-85-6
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: UFXIZCQEFAYYDJ-XPLNXOJDSA-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,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol 在 10% palladium hydroxide on charcoal 、 三氟化硼乙醚 、 氢气 、 sodium hydride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.92h， 生成 (3R,4S,5R,6R)-6-((R)-1-acetoxy-2-(benzyloxy)ethyl)-4,5-bis(benzyloxy)-3-(3-(p-tolyl)propyl)tetrahydro-2H-pyran-2-yl acetate
  参考文献：
  名称：

  在碳水化合物底物上的级联“ Prins-Pinacol型重排和C4-OBn参与”：桥联三环缩酮，环状糖和C2分支庚糖的合成

  摘要：

  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。

  DOI：

  10.1002/chem.201604902
• 作为产物：
  描述：

  溴乙烯 、 3,4,6-tri-O-benzyl-D-glucal epoxide 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 (2β,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  D-葡萄糖和 D-半乳糖与作为糖苷酶抑制剂的吡咯烷亚氨基糖的杂合体的合成

  摘要：

  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。

  DOI：

  10.1002/ejoc.200800770

文献信息

• Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
  作者：Carlos A. Sanhueza、Carlos Mayato、Rubén P. Machı´n、José M. Padrón、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2007.04.060

  日期：2007.7

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.
• C-Glycosides to fused polycyclic ethers
  作者：Shawn P. Allwein、Jason M. Cox、Brett E. Howard、Henry W.B. Johnson、Jon D. Rainier

  DOI：10.1016/s0040-4020(02)00057-1

  日期：2002.3

  This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Cross-metathesis and ring-closing metathesis of olefinic monosaccharides
  作者：Maarten H.D. Postema、Jared L. Piper

  DOI：10.1016/s0040-4039(02)01617-9

  日期：2002.9

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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 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。