cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 74741-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-(cyclohexylmethoxy)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 74741-49-4
• 化学式: C₄₁H₄₈O₆
• 分子量: 636.829
• InChiKey: CEVWXHFLEZHMLS-WEOXEBIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 Cp₂HfCl₂-2AgClO₄ 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  An a-Selective Glycosylation via Decarboxylation of Mixed Carbonate Catalyzed by the Combination of Lewis Acid and Silver Perchlorate

  摘要：

  DOI：

  10.3987/com-97-s84

文献信息

• A substrate-unspecified glycosylation reaction promoted by copper(II) trifluoromethanesulfonate in benzotrifluoride
  作者：Hidetoshi Yamada、Tomomi Hayashi

  DOI：10.1016/s0008-6215(02)00029-0

  日期：2002.4

  A glycosylation reaction induced by copper(II) trifluoromethanesulfonate is described. Using benzotrifluoride as the reaction solvent, five kinds of glycosyl donors, a glucosyl chloride, a fluoride, a trichloroacetimidate, a 1-O-acetyl compound, and a lactol were activated to give the corresponding glucosides.

  描述了由三氟甲磺酸铜（II）诱导的糖基化反应。使用苯并三氟化物作为反应溶剂，将五种糖基供体，葡糖酰氯，氟化物，三氯乙酰亚胺酸酯，1-O-乙酰基化合物和内酯活化，得到相应的葡糖苷。
• A Study of the Rapid Anomerization of Poly-<i>O</i>-benzyl-β-D-glucopyranosides with Titanium Tetrachloride
  作者：Shinkiti Koto、Naohiko Morishima、Reiko Kawahara、Katsuhiko Ishikawa、Shonosuke Zen

  DOI：10.1246/bcsj.55.1092

  日期：1982.4

  Titanium tetrachloride rapidly anomerizes methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside in dichloromethane at 25 °C. Evidence for the proposal that the benzyloxymethyl group on C-5 and the ring oxygen of the glucoside cooperate to prompt the reaction is described. The reagent anomerizes the interglycosidic linkage of several disaccharide derivatives.

  四氯化钛在 25 °C 的二氯甲烷中快速异构化甲基 2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖苷。描述了 C-5 上的苄氧基甲基和糖苷的环氧协同促进反应的证据。该试剂将几种二糖衍生物的糖苷间键异构化。
• A Stereoselective One-stage α-Glucosylation with 2,3,4,6-Tetra-<i>O</i>-benzyl-α-D-glucopyranose and a Mixture of Methanesulfonic Acid, Cobalt(II) Bromide, and Tetraethylammonium Perchlorate
  作者：Shinkiti Koto、Naohiko Morishima、Shonosuke Zen

  DOI：10.1246/bcsj.55.1543

  日期：1982.5

  A one-stage procedure for the stereoselective α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose and a mixture of methanesulfonic acid, cobalt(II) bromide, and tetraethylammonium perchlorate is described. The mechanism of the glucosylation reaction is discussed.

  醇与 2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖和甲磺酸、溴化钴 (II) 和四乙基高氯酸铵的混合物的立体选择性 α-葡萄糖基化的一步程序是描述。讨论了糖基化反应的机理。
• Novel Dehydrative Glycosidations of 1-Hydroxy Sugars Using a Heteropoly Acid
  作者：Kazunobu Toshima、Hideyuki Nagai、Shuichi Matsumura

  DOI：10.1055/s-1999-2869

  日期：1999.9

  Novel and convenient dehydrative glycosidations of 1-hydroxy glycosyl donors have been developed. Several O-benzylated 1-hydroxy sugars are effectively cross-coupled with a variety of alcohols to give the corresponding O-glycosides in high yields with good α-stereoselectivities by using the heteropoly acid, H4SiW12O40.

  我们开发出了新颖便捷的 1-羟基糖基给体脱水糖苷化反应。通过使用杂多酸 H4SiW12O40，几种 O-苄基化的 1-羟基糖与多种醇有效地交叉偶联，得到相应的 O-糖苷，产量高，δ-立体选择性好。
• Photo-induced glycosylation using reusable organophotoacids
  作者：Ryosuke Iwata、Kanjiro Uda、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c4cc04753b

  日期：——

  The glycosylation reactions of glycosyl trichloroacetimidates and several alcohols using an organophotoacid as an activator under photoirradiation proceeded smoothly to give the corresponding glycosides in high yields.

  糖基三氯乙酰亚胺和几种醇的糖基化反应，在光照条件下使用有机光酸作为活化剂进行，顺利进行，产率较高地得到相应的糖苷。