O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->1)-2,3,4-tri-O-benzyl-α-L-rhamnopyranoside | 120269-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->1)-2,3,4-tri-O-benzyl-α-L-rhamnopyranoside
• 英文别名: (2S,3S,4R,5R,6S)-2-methyl-6-[(2S,3R,4R,5S,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 120269-13-8
• 化学式: C₅₄H₅₈O₉
• 分子量: 851.049
• InChiKey: JCIPGGDBHOOIBY-FWFRWICWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  63
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->1)-2,3,4-tri-O-benzyl-α-L-rhamnopyranoside 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 以100%的产率得到Rha(a1-1a)Rha
  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：

  2,3,4-三-O-苄基-L-吡喃鼠李糖 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以98%的产率得到O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->1)-2,3,4-tri-O-benzyl-α-L-rhamnopyranoside
  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

• Synthesis of<i>β</i>-D-Ribofuranosyl-(1→3)-<i>α</i>-L-rhamnopyranosyl-(1→3)-L-rhamnopyranose by in situ Activating Glycosylation Using 1-OH Sugar Derivative and Me₃SiBr–CoBr₂–Bu₄NBr–Molecular Sieves 4A System
  作者：Motoko Hirooka、Yoko Mori、Akiko Sasaki、Shinkiti Koto、Yoshika Shinoda、Aya Morinaga

  DOI：10.1246/bcsj.74.1679

  日期：2001.9

  β-d-Ribofuranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-l-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28,1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-l-rhamnosides.

  β-d-核糖呋喃糖-(1→3)-α-l-鼠李糖琥珀糖-(1→3)-l-鼠李糖，作为C. freundii O28,1c O特异性多糖的三糖重复单元，采用原位活化糖苷化的方法合成，涉及1-OH糖衍生物和三甲基硅基溴、钴(II)溴化物、四丁基溴化铵及4A分子筛的试剂混合物。区域选择性三苯基甲基化对于合成甲基、烯丙基和苄基α-l-鼠李糖苷的3-OH衍生物非常有效。
• Synthesis of Branched-Chain Oligosaccharides in Sarsasaponins by Dehydrative Glycosylation
  作者：Shinkiti Koto、Naohiko Morishima、Masaharu Uchino、Misa Fukuda、Masayo Yamazaki、Shonosuke Zen

  DOI：10.1246/bcsj.61.3943

  日期：1988.11

  The branched-chain oligosaccharides, 6-O-(β-d-glucopyranosyl)-4-O-(α-l-rhamnopyranosyl)-d-glucopyranose, and 2,6-di-O-β-d-glucopyranosyl)-4-O-(α-l-rhamnopyranosyl)-d-glucopyranose, which compose sarsasaponins, as well as the structurally related 2-O-(β-d-glucopyranosyl)-4-O-(α-l-rhamnopyranosyl)-d-glucopyranose were synthesized stepwise via dehydrative glycosylation by a ternary mixture of p-nitrobenzenesulfonyl chloride, silver triflate, and triethylamine.

  组成沙棘皂苷的支链低聚糖、6-O-(β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖和2,6-二-O-β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖，以及结构相似的2-O-(β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖，是通过对硝基苯磺酰氯、三氟甲基磺酸银和三乙胺的三元混合物进行脱水糖基化逐步合成的。
• KOTO, SHINKITI;MORISHIMA, NAOHIKO;UCHINO, MASAHARU;FUKUDA, MISA;YAMAZAKI,+, BULL. CHEM. SOC. JAP., 61,(1988) N1, C. 3943-3950
  作者：KOTO, SHINKITI、MORISHIMA, NAOHIKO、UCHINO, MASAHARU、FUKUDA, MISA、YAMAZAKI,+

  DOI：——

  日期：——
• 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.
• 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。