cyclohexyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside | 92414-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside
• 英文别名: (2S,3R,4R,5R)-2-cyclohexyloxy-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 92414-08-9
• 化学式: C₃₂H₃₈O₅
• 分子量: 502.651
• InChiKey: DZVVPPSGHDFKFO-ANLCFORVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 吡啶 、 4 A molecular sieve 、 lithium perchlorate 、 triphenylmethyl perchlorate 作用下， 生成 cyclohexyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside
  参考文献：
  名称：

  在三苯甲基高氯酸存在下，由相应的 1-O-酰基糖和醇轻松合成 α-葡萄糖苷和 α-核糖苷

  摘要：

  在高氯酸三苯甲基酯存在下，1-O-溴乙酰-β-D-葡萄糖与醇发生立体选择性反应，以良好的收率得到相应的α-葡萄糖苷。1-O-乙酰基-β-D-核糖的类似反应仅提供相应的 β-核糖苷，而在分子筛 4A 和高氯酸锂的存在下，主要以良好的收率制备 α-核糖苷。

  DOI：

  10.1246/cl.1984.907

文献信息

• An Efficient Glycosylation Reaction of 1-Hydroxy Sugars with Various Nucleophiles Using A Catalytic Amount of Activator and Hexamethyldisiloxane
  作者：Teruaki Mukaiyama、Koki Matsubara、Miyuki Hora

  DOI：10.1055/s-1994-25695

  日期：——

  In the presence of hexamethyldisiloxane and anhydrous calcium sulfate, a catalytic amount of activator such as tin(II) trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate , lanthanum trifluoromethanesulfonate or tin(II) chloride smoothly promotes the glycosylation reactions between 1-hydroxy sugars and free alcohols, electron-rich aromatic compounds or silylated nucleophiles to produce various O -, C - or N - glycosides stereoselectively in high yields. In the case of oxygen or nitrogen nucleophiles, β-ribosides are formed, except that α-ribosides are obtained predominantly in the presence of lithium perchlorate. In the case of carbon nucleophiles such as electron-rich aromatic compounds or silyl enol ethers derived from carbonyl compounds, perfect β-selectivity is shown either in the the presence or absence of lithium perchlorate. Further, pyranosyl substrates such as glucose or galactose afford the corresponding α-anomers, except with electron-rich aromatic compounds.

  在六甲基二硅氧烷和无水硫酸钙的存在下，以催化量的活化剂（如二氟三氟甲磺酸锡、三氟三氟甲磺酸镱、三氟三氟甲磺酸镧或二氯化锡）顺利促进1-羟基糖与自由醇、富电子芳香化合物或硅化亲核试剂之间的糖基化反应，高产率地选择性合成各种O-、C-或N-糖苷。对于氧或氮亲核试剂，主要生成β-核糖苷，但在高氯酸锂存在下主要得到α-核糖苷。对于碳亲核试剂（如富电子芳香化合物或来自羰基化合物的硅基烯醇醚），无论在高氯酸锂存在或不存在下，均表现出完全的β-选择性。此外，吡喃糖基底物（如葡萄糖或半乳糖）主要生成相应的α-异构体，但对于富电子芳香化合物则例外。
• Dehydrative glycosylation with cyclic phosphonium anhydrides
  作者：Rajendar Dyapa、Lance T. Dockery、Maciej A. Walczak

  DOI：10.1039/c6ob01812b

  日期：——

  Cyclic phosphonium anhydrides generated from bis-phosphine oxides and trifluoromethanesulfonic anhydride are shown as general coupling reagents in a dehydrative glycosylation reaction of C1-hemiacetals. This reaction protocol is characterized by a broad substrate scope and high yields, including reactions of O-, C-, N-, and S-based nucleophiles with furanose, pyranose, and deoxysugar donors.

  由双膦氧化物和三氟甲磺酸酐生成的环状phospho酸酐显示为C1-半缩醛的脱水糖基化反应中的一般偶联剂。该反应方案的特征在于底物范围广且产率高，包括基于O-，C-，N-和S的亲核试剂与呋喃糖，吡喃糖和脱氧糖供体的反应。
• Synthesis of<i>β</i>-D-Ribofuranosyl-(1→3)-<i>α</i>-L-rhamnopyranosyl-(1→3)-L-rhamnopyranose by in situ Activating Glycosylation Using 1-OH Sugar Derivative and Me₃SiBr–CoBr₂–Bu₄NBr–Molecular Sieves 4A System
  作者：Motoko Hirooka、Yoko Mori、Akiko Sasaki、Shinkiti Koto、Yoshika Shinoda、Aya Morinaga

  DOI：10.1246/bcsj.74.1679

  日期：2001.9

  β-d-Ribofuranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-l-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28,1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-l-rhamnosides.

  β-d-核糖呋喃糖-(1→3)-α-l-鼠李糖琥珀糖-(1→3)-l-鼠李糖，作为C. freundii O28,1c O特异性多糖的三糖重复单元，采用原位活化糖苷化的方法合成，涉及1-OH糖衍生物和三甲基硅基溴、钴(II)溴化物、四丁基溴化铵及4A分子筛的试剂混合物。区域选择性三苯基甲基化对于合成甲基、烯丙基和苄基α-l-鼠李糖苷的3-OH衍生物非常有效。
• Trityl Salt Catalyzed Stereoselective Glycosylation of Alcohols with 1-Hydroxyribofuranose
  作者：Hiromi Uchiro、Teruaki Mukaiyama

  DOI：10.1246/cl.1996.79

  日期：1996.1

  presence of a catalytic amount of several trityl salts, 2,3,5-tri-O-benzyl-D-ribofuranose smoothly reacted with alcohols to give various β-ribofuranosides in high yields with high stereoselectivity while reversed stereoselectivity was observed in the coexistence of lithium perchlolate.

  在催化量的几种三苯甲基盐的存在下，2,3,5-三-O-苄基-D-呋喃核糖与醇顺利反应，以高收率和高立体选择性得到各种β-呋喃核糖苷，同时观察到反向立体选择性高氯酸锂共存。
• A Convenient Method for the Preparation of Disaccharides by Transglycosylation of Methyl Glycosides
  作者：Hiromi Uchiro、Nobuyuki Kurusu、Teruaki Mukaiyama

  DOI：10.1002/ijch.199700011

  日期：——

  Transglycosylation of methyl glycosides with various glycosyl acceptors using a Sn(OTf)2–Me3SiCl promoter system in the presence of molecular sieves 5A afforded the corresponding glycosides. Several useful disaccharides are effectively prepared in good yields with moderate to good stereoselectivities.

  在分子筛5A存在下，使用Sn（OTf）2 -Me 3 SiCl启动子系统将甲基糖苷与各种糖基受体进行转糖基化反应，得到相应的糖苷。几种有用的二糖可以高产率有效制备，具有中等至良好的立体选择性。