benzyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside | 79698-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,6S)-3,4-diacetyloxy-6-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 79698-05-8
• 化学式: C₁₉H₂₄O₈
• 分子量: 380.395
• InChiKey: KJHXBOYEIVHIQV-YRXWBPOGSA-N

物化性质

• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 benzyl 2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  A convenient synthesis of 2-deoxy-d-arabino-hexose and of its methyl and benzyl glycosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)81880-7
• 作为产物：
  描述：

  benzyl 2-S-acetyl-3,4,6-tri-O-acetyl-2-thio-α-D-galactopyranoside 在 一水合肼 、 tris(2,2'-bipyridyl)ruthenium dichloride 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81 %的产率得到benzyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Visible-Light-Promoted Desulfurization to Synthesize Deoxyglycosides

  摘要：

  DOI：

  10.1021/acs.joc.3c00046

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。
• Stereoselective Synthesis of α-Linked 2-Deoxy Glycosides Enabled by Visible-Light-Mediated Reductive Deiodination
  作者：Hao Wang、Jinyi Tao、Xinpei Cai、Wei Chen、Yueqi Zhao、Yang Xu、Wang Yao、Jing Zeng、Qian Wan

  DOI：10.1002/chem.201405516

  日期：2014.12.22

  2‐Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2‐deoxy‐glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2‐deoxy‐α‐glycosides by glycosylation of 2‐iodo‐glycosyl acetate and subsequent visible‐light‐mediated tin‐free reductive deiodination. We have successfully applied

  2-脱氧糖及其衍生物大量存在于许多重要的天然药物中。然而，具体的2-脱氧糖苷键的构建仍然是一个挑战。在此，我们报告了一种通过2-碘-糖基乙酸乙酸酯的糖基化和随后的可见光介导的无锡还原脱碘来制备2-脱氧-α-糖苷的有效方法。我们已成功地将糖基化后去碘化策略应用于30多种单糖，二糖，三糖，四糖和十五糖的合成，并具有出色的立体选择性和效率。该方法也已用于合成包含四个α-键的2-脱氧四糖。
• Practical synthesis of 2-deoxy sugars <i>via</i> metal free deiodination reactions
  作者：Wang Yao、Hao Wang、Jing Zeng、Qian Wan

  DOI：10.1080/07328303.2021.2015365

  日期：2021.11.22

  Abstract 2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction by using cyclohexane and ethyl acetate as co-solvent is reported. This is an environmentally benign protocol, which operates smoothly under

  摘要 2-脱氧糖苷，其中 C-2 羟基被氢原子取代，是许多生物活性天然产物和药物分子中的重要基序。本文报道了一种使用环己烷和乙酸乙酯作为共溶剂的改进的过氧化二月桂酰介导的自由基脱碘反应。这是一种对环境无害的方案，可在温和条件下平稳运行，并允许以高达 98% 的收率有效制备一系列 2-脱氧糖苷。
• Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst
  作者：Ornelio Rosati、Massimo Curini、Federica Messina、Maria Carla Marcotullio、Giancarlo Cravotto

  DOI：10.1007/s10562-012-0932-z

  日期：2013.2

  conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.Graphical Abstract

  层状 α-磺基苯基膦酸锆 - 甲膦酸是一种固体酸催化剂，可在温和的反应条件下，在短时间内和良好的产率催化 d-乙二醇和醇类亲核试剂的费里尔重排。值得注意的是，α-磺基苯基膦酸锆-甲膦酸锆和溴化锂的组合改变了该过程的区域选择性，以良好的收率提供了 2-脱氧糖。
• New reductive deiodination reaction by hydrogen atom transfer from cyclohexane
  作者：Jean Boivin、Béatrice Quiclet-Sire、Laure Ramos、Samir Z. Zard

  DOI：10.1039/a607459f

  日期：——

  Secondary iodides flanked by one or more inductive electron-withdrawing groups can be reduced via a radical chain reaction involving a hydrogen atom transfer from cyclohexane, the process being triggered by a small amount of an initiator such as dilauroyl peroxide.

  次级碘化物两侧有一个或多个诱导性电子吸引基团，可通过自由基链式反应进行还原，该反应涉及从环己烷转移一个氢原子，该过程由少量引发剂（如过氧化二月桂酰）引发。