O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cholesterol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cholesterol
• 英文别名: O-[2,3,4-tri-O-benzyl-β-L-fucopyranosyl]cholesterol；cholesteryl 2,3,4-tri-O-benzyl-α-L-fucopyranoside；(2R,3S,4R,5R,6S)-2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-methyl-3,4,5-tris(phenylmethoxy)oxane
• 化学式: C₅₄H₇₄O₅
• 分子量: 803.179
• InChiKey: LBKUVZPETAEEPZ-YMCVTWOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 四溴化碳 、 三苯基膦 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cholesterol
  参考文献：
  名称：

  An easy access to halide ion-catalytic α-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional reagents

  摘要：

  2-O-苄基-1-羟基糖与CBr4和Ph3P反应生成一种即时的糖基溴化物，该溴化物在N,N-四甲基脲存在下与受体醇耦合，几乎定量地得到α-糖基产物。在提出的反应途径中，试剂组合扮演了多个角色，如糖基供体的生成、糖基化的活化以及反应体系的脱水作用。这些角色使得一个简单的α-糖基化反应得以进行，而无需特别关注脱水步骤。利用这种方法已经制备了多种α-糖基（D-葡萄糖、D-半乳糖和L-岩藻糖）产物，包括糖基甘油和胆固醇。

  DOI：

  10.1039/b303984f

文献信息

• An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
  作者：An-Hsiang Adam Chu、Andrei Minciunescu、Vittorio Montanari、Krishna Kumar、Clay S. Bennett

  DOI：10.1021/ol5004059

  日期：2014.3.21

  iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background

  空气和水稳定的碘鎓盐苯基（三氟乙基）碘鎓三氟甲磺酰亚胺在室温下可激活硫代糖苷以进行糖基化。武装和解除武装的硫糖苷都以 68-97% 的产率迅速进行糖基化。反应条件温和，不需要严格排除空气和水分。该方法的操作简单性应该允许具有有限合成背景的实验者构建糖苷键。
• Glycosylation Reactions Using Phenyl(trifluoroethyl)iodonium Salts
  申请人：Trustees of Tufts College

  公开号：US20150099870A1

  公开（公告）日：2015-04-09

  Provided are methods for the preparation of glycosylation products, including those represented by formula I: Sugar-O—R′  I comprising the step of combining R′—OH, a glycosyl sulfide glycosyl donor (“thioglycoside donor”), a hypervalent iodine alkyl-transfer activating reagent, and a base. In an embodiment, the hypervalent iodine alkyl-transfer activating reagent is (phenyl(trifluoroethyl)iodonium triflimide).

  提供了制备糖基化产物的方法，包括由式I表示的那些： 糖-O—R′  I 包括将R′—OH、糖基硫醚糖基供体（“硫代糖苷供体”）、高价碘烷基转移活化试剂和碱结合的步骤。在一种实施例中，高价碘烷基转移活化试剂为（苯基(三氟乙基)碘三氟甲磺酰胺）。
• One-Pot α-Glycosylation Method Using Appel Agents in <i>N,N</i>-Dimethylformamide
  作者：Yoshihiro Nishida、Yuko Shingu、Hirofumi Dohi、Kazukiyo Kobayashi

  DOI：10.1021/ol034269+

  日期：2003.7.1

  graphicA concept for the development of practical glycosylation is presented and demonstrated by one-pot alpha-glycosylation applying Appel agents for 2-O-benzyl-1-OH hexoses in DMF. The reaction, in situ giving the equilibrium of glycosyl bromides and more reactive O-glycoside intermediates, accomplishes a near-quantitative alpha-glycosylation removing the water molecules.
• An easy access to halide ion-catalytic α-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional reagents
  作者：Yuko Shingu、Yoshihiro Nishida、Hirofumi Dohi、Kazukiyo Kobayashi

  DOI：10.1039/b303984f

  日期：——

  The reaction of a 2-O-benzyl-1-hydroxy sugar with CBr4 and Ph3P generates a glycosyl bromide in situ, which is coupled with an acceptor alcohol in the presence of N,N-tetramethylurea to afford an α-glycosyl product virtually quantitatively. In a proposed pathway, the reagent combination plays multiple roles such as the generation of a glycosyl donor, the activation of glycosylation, and the dehydration of the reaction system. These roles allow a simple α-glycosylation to be performed without special attention to dehydration. Various α-glycosyl (D-gluco-, D-galacto- and L-fuco-) products including glycosyl glycerols and cholesterols have been prepared with this method.

  2-O-苄基-1-羟基糖与CBr4和Ph3P反应生成一种即时的糖基溴化物，该溴化物在N,N-四甲基脲存在下与受体醇耦合，几乎定量地得到α-糖基产物。在提出的反应途径中，试剂组合扮演了多个角色，如糖基供体的生成、糖基化的活化以及反应体系的脱水作用。这些角色使得一个简单的α-糖基化反应得以进行，而无需特别关注脱水步骤。利用这种方法已经制备了多种α-糖基（D-葡萄糖、D-半乳糖和L-岩藻糖）产物，包括糖基甘油和胆固醇。