octa-O-benzyl-β,β-trehalose | 25018-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octa-O-benzyl-β,β-trehalose
• 英文别名: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside；(2R,3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
• CAS: 25018-28-4
• 化学式: C₆₈H₇₀O₁₁
• 分子量: 1063.3
• InChiKey: AVZQUDHQXONDDN-CELDWKOKSA-N

物化性质

• 熔点：
  121 °C
• 密度：
  1.24±0.1 g/cm3(Predicted)

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：

  octa-O-benzyl-β,β-trehalose 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 beta-D-吡喃葡萄糖基beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis and Glycosylation Shift of 1,1'-Disaccharides.

  摘要：

  Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.

  DOI：

  10.1248/cpb.42.982
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以44%的产率得到2,3,4,6,2',3',4',6'-octa-O-benzyl-α,β-trehalose
  参考文献：
  名称：

  TMS三氟甲磺酸酯诱导了从1-羟基糖合成1,1'-二糖。

  摘要：

  通过TMS三氟甲磺酸诱导1-羟基糖的偶联反应，制备了多种1,1'-二糖，产率尚可。

  DOI：

  10.1248/cpb.42.2400

文献信息

• Molecular sieves promote stereocontrolled αα-disaccharide formation via direct dimerization of free sugars
  作者：Gary H. Posner、D.Scott Bull

  DOI：10.1016/0040-4039(96)01376-7

  日期：1996.8

  Some commercial molecular sieves promote direct dimerization of free pyranose and furanose sugars stereoselectively into the corresponding α,α-disaccharides.

  一些商业分子筛促进游离的吡喃糖和呋喃糖糖立体选择性地直接二聚为相应的α，α-二糖。
• TMS Triflate Induced Synthesis of 1,1'-Disaccharides from 1-Hydroxy Sugars.
  作者：Mugio NISHIZAWA、Dulce M. GARCIA、Yohko NOGUCHI、Kumiko KOMATSU、Susumi HATAKEYAMA、Hidetoshi YAMADA

  DOI：10.1248/cpb.42.2400

  日期：——

  A variety of 1, 1'-disaccharides have been prepared by TMS triflate induced coupling of 1-hydroxy sugars in reasonable yield.

  通过TMS三氟甲磺酸诱导1-羟基糖的偶联反应，制备了多种1,1'-二糖，产率尚可。
• Synthesis and Glycosylation Shift of 1,1'-Disaccharides.
  作者：Mugio NISHIZAWA、Shinichi KODAMA、Yoshie YAMANE、Kiyoko KAYANO、Susumi HATAKEYAMA、Hidetoshi YAMADA

  DOI：10.1248/cpb.42.982

  日期：——

  Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.
• 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.