methyl 3-O-allyl-2,4-di-O-benzyl-α-L-rhamnopyranoside | 135041-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-allyl-2,4-di-O-benzyl-α-L-rhamnopyranoside
• 英文别名: (2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)-4-prop-2-enoxyoxane
• CAS: 135041-31-5
• 化学式: C₂₄H₃₀O₅
• 分子量: 398.499
• InChiKey: NIWZXZSYFPIGKZ-ZNKILWFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-O-allyl-2,4-di-O-benzyl-α-L-rhamnopyranoside 在 三氟化硼乙醚 硫酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 (2R,3R,4R,5R,6S)-2-methoxy-6-methyl-3-[(2S,3R,4R,5S,6S)-6-methyl-3,5-bis(phenylmethoxy)-4-prop-2-enoxyoxan-2-yl]oxy-4,5-bis(phenylmethoxy)oxane
  参考文献：
  名称：

  立体聚合法合成鸟分枝杆菌血清型4的糖肽脂抗原的寡糖片段：在获得性免疫缺陷综合征患者中观察到的主要血清变异

  摘要：

  描述了一种立体收敛方法，用于血清型4的糖肽脂质抗原的寡糖片段，通常在AIDS患者中发生。

  DOI：

  10.1016/0040-4039(91)80786-6
• 作为产物：
  描述：

  L-rhamnopyranose 在 吡啶 、 甲醇 、 甲烷磺酸 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.25h， 生成 methyl 3-O-allyl-2,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis ofβ-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-L-rhamnopyranose by in situ Activating Glycosylation Using 1-OH Sugar Derivative and Me₃SiBr–CoBr₂–Bu₄NBr–Molecular Sieves 4A System

  摘要：

  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。

  DOI：

  10.1246/bcsj.74.1679

文献信息

• A novel approach for stereochemical analysis of 1-carboxyethyl sugar ethers by NMR spectroscopy
  作者：Wayne B. Severn、James C. Richards

  DOI：10.1021/ja00056a041

  日期：1993.2

  A general strategy for the stereochemical analysis of 1-carboxyethyl sugar ethers is introduced in which the chirality of the lactyl group is related to that of the sugar moiety in a conformationally rigid lactone derivative. With the aid of molecular modeling, the stereochemistry is determined through the use of NOE measurements. This procedure was evaluated using synthetic diastereomeric samples

  介绍了 1-羧乙基糖醚立体化学分析的一般策略，其中乳基的手性与构象刚性内酯衍生物中糖部分的手性有关。在分子建模的帮助下，立体化学是通过使用 NOE 测量来确定的。该程序使用 (R)- 和 (S)-甲基 3-O-(1-羧乙基)-α-L-吡喃鼠李糖苷的合成非对映体样品进行评估，并成功应用于 N-乙酰胞壁酸的立体化学分析
• Selective 3-O-allylation and 3-O-benzylation of methyl α-d-manno-, α-l-rhamno- and β-l-fuco-pyranoside
  作者：Guangbin Yang、Fanzuo Kong、Shuhua Zhou

  DOI：10.1016/0008-6215(91)84158-b

  日期：1991.4
• Synthesis of methyl 3--[3--(2,3,4-tri--methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside : The outer trisaccharide unit of a unique glycopeptidolipid
  作者：Mukund K Gurjar、Anupama S Mainkar

  DOI：10.1016/s0040-4020(01)80018-1

  日期：1992.1

  The combination of sugars present in Mycobacterium xenopi glycopeptidolipid (GPL X-1) has been characterised as O-(2,3,4-tri-O-methyl-alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-6-deoxy-L-glucose. Two synthetic routes (A and B) towards the outer trisaccharide segment (2) have been designed. Route A involved the condensation of the aglycone (7) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl bromide (13) to afford which was sequentially deacetylated, methylated, deallylated and reacetylated to afford 12. Condensation of 12 with 16 in the presence of borontrifluoride etherate was unsuccessful. In route B, the disaccharide 21 was synthesised by the coupling reaction between 16 and 18 in the presence of borontrifluoride-etherate followed by deallylation. Alternatively, the disaccharide triacetate (22) was first prepared and routine modifications on it led to the formation of 21. Final condensation of 21 with the trichloroacetimidate (29) followed by sequential deacetylation, methylation and debenzylation afforded the trisaccharide (2).
• YANG, GUANGBIN;KONG, FANZUO;ZHOU, SHUHUA, CARBOHYDR. RES., 211,(1991) N, C. 179-182
  作者：YANG, GUANGBIN、KONG, FANZUO、ZHOU, SHUHUA

  DOI：——

  日期：——
• 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。