1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-α-D-galactopyranoside | 71024-09-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-α-D-galactopyranoside
• 英文别名: 1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-α-D-galactopyranose；1-(1':2',3':4'-di-O-isopropylidene-galacto-α-D-hexopyranosyl)-(1->6)-2,6-dideoxy-3,4-di-O-acetyl-α-L-arabinohexopyranoside；1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2-deoxy-α-L-rhamnopyranosyl)-α-D-galactopyranoside；[(2S,3S,4S,6R)-3-acetyloxy-2-methyl-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-4-yl] acetate
• CAS: 71024-09-4
• 化学式: C₂₂H₃₄O₁₁
• 分子量: 474.505
• InChiKey: UJPJSXHOIYNHNL-LKRITGDSSA-N

物化性质

• 沸点：
  528.3±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Convenient Iodonium-Promoted Stereoselective Synthesis of 2-Deoxy-α-glycosides by Use ofS-(2-Deoxyglycosyl) Phosphorodithioates as Donors

  摘要：

  S-(2-脱氧糖基)O,O-二乙基二硫代磷酸酯很容易从糖醛中获得，是在 N-碘代琥珀酰亚胺或双(2,4,6-三甲基吡啶)高氯酸碘鎓等促进剂存在下进行糖基化的方便前体。在一系列的转化中，α- 和 β-糖基供体都立体选择性地连接到受体糖分子 [1,2: 3,4-二-O-异丙叉-α-D-吡喃半乳糖 (1)，苄基 3- O-苄基-2,6-二脱氧-β-L-核糖-吡喃己糖苷 (2) 或苄基 4-O-苄基-2,6-二脱氧-β-L-核糖-吡喃糖苷 (3)] 在主要和次要位置反应时间短且产率普遍令人信服。

  DOI：

  10.1055/s-1992-26321

文献信息

• Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
  作者：Gaoyuan Zhao、Ting Wang

  DOI：10.1002/anie.201800909

  日期：2018.5.22

  The direct, photoacid‐catalyzed synthesis of 2‐deoxyglycosides from glycals is reported. A series of phenol‐conjugated acridinium‐based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford

  据报道，由糖类直接，光酸催化合成了2-脱氧糖苷。与市售的酚催化剂曙红Y一起，合理设计，合成和研究了一系列基于酚共轭啶基的有机光酸。在这种光酸催化剂和光的存在下，合成糖被活化并与多种醇偶联以高收率和优异的α-选择性提供2-脱氧糖苷。
• Stereoselective synthesis of α-linked 2-deoxysaccharides and furanosaccharides by use of 2-deoxy 2-pyridyl-1-thio pyrano- and furanosides as donors and methyl iodide as an activator
  作者：Hari Babu Mereyala、Vinayak R Kulkarni、D Ravi、GVM Sharma、B Venkateswara Rao、G Bapu Reddy

  DOI：10.1016/s0040-4020(01)89016-5

  日期：——

  A practical and highly stereoselective glycosidation methodology is described, where anomeric mixture of 2-deoxy 2-pyridyl-1-thiopyranoside donors (1–3, 27) have been coupled with several sugar alcohols (4–8,29,31) on activation by methyl iodide to obtain axially linked 2-deoxysaccharides (9–17,30,32,33). Application of this method for the synthesis of disaccharide fragment 28 of avermectin is also

  一种实用的和高立体选择性糖苷化的方法进行了说明，其中2-脱氧-2-吡啶基-1- thiopyranoside供体（的端基异构混合物1-3，27）已经被加上几个糖醇（4-8,29,31）上激活通过甲基碘获得轴向连接的2-脱氧糖（9–17,30,32,33）。还描述了该方法在合成阿维菌素的二糖片段28中的应用。通过使用2-吡啶基-1-硫呋喃糖苷（34-36）作为供体来制备α-连接的呋喃糖苷（42-51），也显示了该方法的实用性。
• A mild general method for the synthesis of ∝-2-deoxy-disaccharides: Synthesis of L-oleandrosyl-L-oleandrose from D-glucose
  作者：D. Ravi、Vinayak R. Kulkarni、Hari Babu Mereyala

  DOI：10.1016/s0040-4039(01)80712-7

  日期：1989.1

  A mild, general method for the stereoselective synthesis of ∝-2-deoxy disaccharides is described using 2-deoxy-2-pyridyl 1-thioglycosides 4, 7, 8 as glycosyl donors and methyl iodide as an activator. Thus, a disaccharide 6 component of avermectin family is synthesized starting from D-glucose.

  对于α-2-脱氧二糖的立体选择性合成一种温和，一般方法描述了使用2-脱氧-2-吡啶基1-硫代糖苷4，7，8为糖基供体和甲基碘作为活化剂。因此，从D-葡萄糖开始合成阿维菌素家族的二糖6成分。
• Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors
  作者：Anjali Aghi、Sankar Sau、Amit Kumar

  DOI：10.1016/j.carres.2024.109051

  日期：2024.2

  Herein, we report a mild and economical route for the stereoselective synthesis of 2-deoxy and 2,6-dideoxyglycosides FeCl-catalyzed activation of bench stable deoxy-phenylpropiolate glycosyl donors (D-PPGs). Optimized reaction conditions work well under additive-free conditions to afford the corresponding 2-deoxy and 2,6-dideoxyglycosides in good yields with high α-anomeric selectivity by reacting

  在此，我们报道了一种温和且经济的路线，用于立体选择性合成 2-脱氧和 2,6-二脱氧糖苷 FeCl 催化活化工作台稳定的脱氧苯丙炔酸糖基供体 (D-PPG)。优化的反应条件在无添加剂的条件下运行良好，通过与糖和非糖基受体反应，以良好的收率和高 α-异头选择性提供相应的 2-脱氧和 2,6-二脱氧糖苷。优化的条件也适用于解除武装的 D-PPG 捐赠者。此外，所开发的策略适合大规模合成。
• Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using <i>S</i>-But-3-ynyl Thioglycoside Donors
  作者：Surya Adhikari、Kedar N. Baryal、Danyang Zhu、Xiaohua Li、Jianglong Zhu

  DOI：10.1021/cs300670k

  日期：2013.1.4

  A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy alpha-glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2-deoxy and 2,6-dideoxy thioglycoside donors were able to react with a variety of primary, secondary, and tertiary alcohol acceptors to afford alpha-selective glycosides in good to excellent yields.