(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside | 74080-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
• CAS: 74080-40-3
• 化学式: C₆₈H₇₀O₁₁
• 分子量: 1063.3
• InChiKey: AVZQUDHQXONDDN-FSRATHDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  79
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 α-D-Galactopyranosyl α-D-galactopyranoside
  参考文献：
  名称：

  新式合成糖苷。合成的α，α-海藻糖，类似物半乳糖，甘露等-α-d-糖苷

  摘要：

  摘要在三氟甲磺酸（三氟甲磺酸）酐为催化剂，二氯甲烷为溶剂的情况下，在低温下存在2,3,4,6-四-O-苄基-d-吡喃葡萄糖，2,3,4,6-四-O -苄基-d-吡喃半乳糖和2,3,4,6-四-O-苄基-d-甘露吡喃糖几乎定量地转化为相应的α，α-（1→1）和2：1混合物α，β-（1→1）二糖。因此，在柱后，获得了α，α-海藻糖的纯2,3,4,6,2'，3'，4'，6-辛基-O-苄基衍生物，以及d-半乳糖和d-甘露糖类似物。层析，产率55-65％。氢解得到相应的游离糖。以10–34％的产率获得纯的异头物。该方法的潜力通过合成2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖基2,3：4,5-二-O-异亚丙基-β-d-果糖吡喃糖苷来证明。 50％的产量，

  DOI：

  10.1016/s0008-6215(00)85133-2
• 作为产物：
  描述：

  1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  全苄基α,α-海藻糖及其D-半乳糖和D-甘露糖类似物的高度立体选择性合成

  摘要：

  用三甲基甲硅烷基三氟甲磺酸酯催化剂在二氯甲烷中处理 2,3,4,6-四-邻苄基-1-邻三甲基甲硅烷基-α,β-D-吡喃葡萄糖，定量得到相应的α,α-和α,β-海藻糖屈服。D-半乳糖和 D-甘露糖类似物的类似处理分别只产生相应的 α,α-异头物。

  DOI：

  10.1246/cl.1983.319

文献信息

• Dehydrative Glycosylation with the Hendrickson Reagent
  作者：Matteo Mossotti、Luigi Panza

  DOI：10.1021/jo2015856

  日期：2011.11.4

  The Hendrickson reagent is able to perform efficiently dehydrative glycosylation of 1-hydroxyglycosyl donors. The reaction occurs under mild conditions through an anomeric oxophosphonium intermediate detected by nuclear magnetic resonance. Further insight into the mechanism was gained by 18O labeling of anomeric OH.

  亨德里克森试剂能够有效地进行1-羟基糖基供体的脱水糖基化。该反应在温和条件下通过核磁共振检测到的异头氧代intermediate中间体而发生。通过18 O标记异头OH获得了对该机理的进一步了解。
• Nouvelle méthode de synthèse Stéréosélective de glycosides. Syntèse des α,α-tréhalose, analogues galacto, manno et autres α-d-glycosides
  作者：André A. Pavia、Jean-Michel Rocheville、Sak N. Ung

  DOI：10.1016/s0008-6215(00)85133-2

  日期：1980.2

  corresponding α,α-(1 → 1) and α,β-(1 → 1) disaccharides. Hence, pure 2,3,4,6,2′,3′,4′,6 - octa-O-benzyl derivatives of α,α-trehalose, and the d -galacto and d -manno analogues were obtained, after column chromatography, in 55–65% yield. Hydrogenolysis gave the corresponding free sugars. The pure anomers were obtained in 10–34% yield. The potentiality of the method was demonstrated by the synthesis of 2,3

  摘要在三氟甲磺酸（三氟甲磺酸）酐为催化剂，二氯甲烷为溶剂的情况下，在低温下存在2,3,4,6-四-O-苄基-d-吡喃葡萄糖，2,3,4,6-四-O -苄基-d-吡喃半乳糖和2,3,4,6-四-O-苄基-d-甘露吡喃糖几乎定量地转化为相应的α，α-（1→1）和2：1混合物α，β-（1→1）二糖。因此，在柱后，获得了α，α-海藻糖的纯2,3,4,6,2'，3'，4'，6-辛基-O-苄基衍生物，以及d-半乳糖和d-甘露糖类似物。层析，产率55-65％。氢解得到相应的游离糖。以10–34％的产率获得纯的异头物。该方法的潜力通过合成2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖基2,3：4,5-二-O-异亚丙基-β-d-果糖吡喃糖苷来证明。 50％的产量，
• Formation of O-Glycosidic Linkages from 1-Hydroxy Sugars by Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation
  作者：Takashi Yamanoi、Ryo Inoue、Sho Matsuda、Kazuya Iwao、Yoshiki Oda、Akihiro Yoshida、Keita Hamasaki

  DOI：10.3987/com-08-s(f)41

  日期：——

  This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux temperature for 15 min in dichloromethane afforded O-glycosides in good yields. An 1,6-anhydro-beta-D-glucopyranosidic linkage was formed by the intramolecular condensation of the corresponding 1-hydroxy sugar performed with similar reaction conditions using 5 mol% bismuth(III) triflate. A reaction using 10 mol% bismuth(III) triflate at room temperature in dichloromethane promoted the self- or cross-condensations of I-hydroxy sugars to produce several kinds of 1,1'-disaccharides. This paper reports some important properties of bismuth(III) triflate catalyzed dehydrative glycosidation using 1-hydroxy sugars to form various O-glycosidic linkages.
• A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin
  作者：Darren Gibson、Steven W. Homans、Robert A. Field

  DOI：10.1016/j.tetasy.2009.02.021

  日期：2009.5

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.
• THE HIGHLY STEREOSELECTIVE SYNTHESIS OF PERBENZYLATED α,α-TREHALOSE AND ITS D-<i>GALACTO</i>AND D-<i>MANNO</i>ANALOGS
  作者：Juji Yoshimura、Kazutoshi Hara、Tatsuya Sato、Hironobu Hashimoto

  DOI：10.1246/cl.1983.319

  日期：1983.3.5

  6-tetra-o-benzyl-1-o-trimethylsilyl-α,β-D-glucopyranose in dichloromethane with trimethylsilyl triflate catalyst gave the corresponding α,α- and α,β-trehaloses in quantitative yield. A similar treatment of D-galacto and D-manno analogs gave exclusively the corresponding α,α-anomers, respectively.

  用三甲基甲硅烷基三氟甲磺酸酯催化剂在二氯甲烷中处理 2,3,4,6-四-邻苄基-1-邻三甲基甲硅烷基-α,β-D-吡喃葡萄糖，定量得到相应的α,α-和α,β-海藻糖屈服。D-半乳糖和 D-甘露糖类似物的类似处理分别只产生相应的 α,α-异头物。