methyl 6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-arabino-hept-2-enit-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-pyranoside | 232603-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-arabino-hept-2-enit-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-pyranoside
• 英文别名: (2R,3S,4R)-6-[2-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethyl]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 232603-20-2
• 化学式: C₅₆H₆₀O₉
• 分子量: 877.087
• InChiKey: MHMNTDIVXULCBB-DCMGSSPYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  891.448±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.217±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-arabino-hept-2-enit-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-pyranoside 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以73%的产率得到methyl 6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-pyranoside
  参考文献：
  名称：

  An Olefin Metathesis Route for the Preparation of (1→6)-Linked C-Disaccharide Glycals. A Convergent and Flexible Approach to C-Saccharide Synthesis

  摘要：

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

  DOI：

  10.1021/jo0005159
• 作为产物：
  描述：

  methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 Lindlar's catalyst 、 <(F3C)2MeCO>2Mo=N(2,6-iPr2Ph)(=CHCMe2Ph) 4-二甲氨基吡啶 、 lithium hydroxide 、 四甲基乙二胺 、 氢气 、 四氯化钛 、 N,N'-二环己基碳二亚胺 、 lead(II) chloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 methyl 6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-arabino-hept-2-enit-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-pyranoside
  参考文献：
  名称：

  通过烯烃复分解聚合制备1,6-连接的C-二糖

  摘要：

  3,4,6-三-O-苄基-1,2-二脱氧-d-阿拉伯糖基-己-1-烯醇（5a）与多种糖基羧酸6a-d的DCC介导的偶联反应得到酯7a -d的产量高。形成的酯的亚甲基化导致无环烯醇醚8a-d，并在盒子中在温暖的甲苯中暴露于Schrock钼催化剂1中，以良好的产率得到目标C-二糖二醇9a-d。将1，6-连接的基于葡萄糖的C-二糖聚糖9a转化为2-脱氧-β-葡萄糖衍生物10a以及相应的葡萄糖β-葡萄糖-C-二糖13。

  DOI：

  10.1016/s0040-4039(99)00815-1

文献信息

• A Pd-Catalyzed Approach to (1→6)-Linked <i>C</i>-Glycosides
  作者：Dennis C. Koester、Markus Leibeling、Roman Neufeld、Daniel B. Werz

  DOI：10.1021/ol101625p

  日期：2010.9.3

  (1→6)-linked C-glycosidic disaccharides is presented. The key reaction is a Pd-catalyzed coupling of 1-iodo- or 1-triflato-glycals with alkynyl glycosides. Reinstallation of the native hydroxyl group pattern is achieved after selective hydrogenation of the triple bond using Raney-nickel. Epoxidation with DMDO and reductive epoxide opening gives access to either the α- or the β-derivative, depending on the hydride

  提出了一种灵活而鲁棒的组装（1→6）连接的C-糖苷二糖的方法。关键反应是Pd催化的1-碘-或1-triflato-糖与炔基糖苷的偶联。使用阮内镍对三键进行选择性加氢后，可以重新安装天然羟基图案。取决于氢化物的来源，使用DMDO和还原性环氧化合物进行的环氧化作用可接触到α或β衍生物。
• Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-<i>C</i>-Disaccharides¹
  作者：Maarten H. D. Postema、Jared L. Piper、Lei Liu、Jie Shen、Marcus Faust、Peter Andreana

  DOI：10.1021/jo030039x

  日期：2003.6.1

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.