cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside | 82252-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside
• 英文别名: cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside；cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside；(2R,3S,4R,6S)-6-cyclohexyloxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 82252-30-0
• 化学式: C₃₃H₄₀O₅
• 分子量: 516.678
• InChiKey: OWDDAYROLXCALF-FYZVQMPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 在 吡啶 、 氢氟酸 、 硫酸酯 、 zirconium(IV) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Novel Stereocontrolled Glycosidations of 2-Deoxyglucopyranosyl Fluoride Using a Heterogeneous Solid Acid, Sulfated Zirconia (SO₄/ZrO₂)

  摘要：

  开发了一种新型立体选择性的2-脱氧-α-D-葡萄糖苷氟化物的糖苷化反应，采用了一种均匀且环保的固体酸——硫酸锆（SO4/ZrO2）。在25°C下，使用SO4/ZrO2在CH3CN中反应1小时，能够主要得到相应的2-脱氧-α-D-葡萄糖苷。而在0°C下，使用SO4/ZrO2与分子筛5A在乙醚中反应1小时，则能选择性地获得相应的2-脱氧-β-D-葡萄糖苷。

  DOI：

  10.1055/s-1999-2742

文献信息

• TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
  作者：Mei-Yuan Hsu、Yi-Pei Liu、Sarah Lam、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3762/bjoc.12.164

  日期：——

  The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。
• Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation
  作者：Titli Ghosh、Ananya Mukherji、Hemant Kumar Srivastava、Pavan K. Kancharla

  DOI：10.1039/c8ob00423d

  日期：——

  A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Brønsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy

  已经公开了利用乳醇官能度的新的有机催化糖基化方法。在强力条件下，通过弱布朗斯台德酸，容易获得的仲胺盐，在强迫条件下由乳糖醇催化生成糖基氧杂碳鎓离子会影响2-脱氧吡喃糖和呋喃糖的非对映选择性糖基化。这种操作简单的亚胺基催化的2-脱氧半缩醛的活化是需要特殊处理的现有繁琐方法的潜在替代方法。基于实验证据和理论研究，已经讨论了这种独特转化和动力学/热力学效应的机理。
• Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate
  作者：Mei-Yuan Hsu、Sarah Lam、Chia-Hui Wu、Mei-Huei Lin、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3390/molecules25051103

  日期：——

  dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

  描述了在微波辐射下由三氟甲磺酸二苯基铵催化的碳水化合物半缩醛的直接脱水糖基化的方法。武装和解除武装的糖基-C1-半缩醛供体均以中等至优异的产率有效糖基化，无需任何干燥剂和化学计量添加剂。该方法已成功应用于固相糖基化。
• 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。
• A NOVEL METHOD FOR THE SYNTHESIS OF 2-DEOXYDISACCHARIDE BY STEREOSELECTIVE CYCLIZATION OF THE ACYCLIC PRECURSOR
  作者：Keisuke Suzuki、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.683

  日期：1982.5.5

  Stereoselective cyclization of (Z)-(2R,3R,4R)-6-cyclohexyloxy-1,3,4-tribenzyloxy-5-hexen-2-ol (1)promoted by Hg(OCOCF3)2, followed by reductive work up gave the 2-deoxy-α-hexopyranoside derivative almost exclusively. On the other hand, a predominant formation of the β-anomer was achieved by the treatment of 1 with PhSeCl, and the successive deselenation.

  在 Hg(OCOCF3)2 的促进下，(Z)-(2R,3R,4R)-6-环己氧基-1,3,4-三苄氧基-5-己烯-2-醇（1）发生立体选择性环化，然后进行还原反应，几乎只得到 2-脱氧-α-己吡喃糖苷衍生物。另一方面，用 PhSeCl 处理 1 并连续进行脱硒反应，可主要生成 β-异构体。