1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2,6-dideoxy-β-L-arabino-hexopyranosyl)-α-D-galactopyranose | 73240-27-4

• 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-β-L-arabino-hexopyranosyl)-α-D-galactopyranose
• 英文别名: 1,2:3,4-di-O-isopropylidene-6-O-(3,4-di-O-acetyl-2,6-dideoxy-β-L-arabino-hexopyranosyl)-α-D-galactopyranoside；1-(1':2',3':4'-di-O-isopropylidene-galacto-α-D-hexopyranosyl)-(1->6)-2,6-dideoxy-3,4-di-O-acetyl-β-L-arabinohexopyranoside；[(2S,3S,4S,6S)-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: 73240-27-4
• 化学式: C₂₂H₃₄O₁₁
• 分子量: 474.505
• InChiKey: UJPJSXHOIYNHNL-UMCLFUTCSA-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-β-L-arabino-hexopyranosyl)-α-D-galactopyranose
  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 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。
• 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.
• Tagged Hypervalent Iodine Reagents:  A New Purification Concept Based on Ion Exchange through S_N2 Substitution
  作者：Eike Kunst、Florian Gallier、Gilles Dujardin、Mekhman S. Yusubov、Andreas Kirschning

  DOI：10.1021/ol702319p

  日期：2007.12.1

  The preparation of phenylsulfonate-tagged iodine(III) reagents as well as their use in a novel purification strategy for iodine(III)-promoted reactions is described. The concept is based on ion exchange and is initiated by an azide-promoted S(N)2-reaction at the alkyl sulfonate followed by trapping of the resulting aryl sulfonate anion with an ion-exchange resin. The concept is successfully proven for Ru-catalyzed oxidations of alcohols, the activation and glycosidation of thioglycosides, and the Suarez reaction of pyranoses.
• Wandzik; Szeja, Polish Journal of Chemistry, 1999, vol. 73, # 7, p. 1163 - 1170
  作者：Wandzik、Szeja

  DOI：——

  日期：——