(2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇 | 150995-11-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
• 英文名称: geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside
• 英文别名: geranyl β-primeveroside；Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 150995-11-2
• 化学式: C₂₁H₃₆O₁₀
• 分子量: 448.511
• InChiKey: IEGFOTASSBZIBZ-QLPUMLPOSA-N

物化性质

• 沸点：
  669.2±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇 在 水 作用下， 反应 1.5h， 生成 β-primeverose 、 香叶醇
  参考文献：
  名称：

  Guo, Wenfei; Yamauchi, Kazuyo; Watanabe, Naoharu, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 5, p. 962 - 964

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-3,7-二甲基-2,6-辛二烯-1-基 BETA-D-吡喃葡萄糖苷 在 盐酸 、 4-二甲氨基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 66.5h， 生成 (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Naturally Occurring Geranyl 6-O-Glycosyl-b-D-glucopyranosides

  摘要：

  DOI：

  10.3987/com-05-10640

文献信息

• Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation
  作者：Tianlu Li、Tong Li、Youqin Zhang、Richard R. Schmidt、Peng Peng

  DOI：10.1021/acs.jafc.1c07043

  日期：2022.2.23

  addition, the influence of molecular sieves was elucidated. With regard to these findings, the serious problem of the competing orthoester formation side reaction was successfully overcome with low catalyst loading (1 mol %) and the use of 5 Å molecular sieves, leading to the preparation of a variety of tea aroma precursor β-d-glucopyranosides and β-primeverosides on a gram scale in high yields in an economical

  茶香前体甙是植物来源的天然产物，具有很大的经济价值。然而，在过去的几十年中，这些糖苷的制备在很大程度上仍然被忽视。在此，我们报告了一种温和、高效且可持续的化学催化工艺，用于生产茶香气前体糖苷。在研究糖苷化过程中，发现催化剂在有利于不同反应途径的产物形成中起决定性作用；此外，阐明了分子筛的影响。关于这些发现，通过低催化剂负载量（1 mol %）和使用 5 Å 分子筛成功克服了竞争性原酸酯形成副反应的严重问题，从而制备了多种茶香气前体 β- d以经济的方式以克级高产量生产吡喃葡萄糖苷和 β-primeverosides。综上所述，目前的方法具有催化糖苷化的特点，采用无毒、低成本的催化剂，具有良好的绿色性和可持续性，有望实现茶香前体糖苷的工业化生产。
• Geranyl 6-O-β-d-xylopyranosyl-β-d-glucopyranoside isolated as an aroma precursor from tea leaves for oolong tea
  作者：Wenfei Guo、Kanzo Sakata、Naoharu Watanabe、Ryuta Nakajima、Akihito Yagi、Kazuo Ina、Shaojun Luo

  DOI：10.1016/0031-9422(93)85093-7

  日期：1993.8

  Abstract A new geranyl glycoside, geranyl 6-O-β- d -xylopyranosyl-β- d -glucopyranoside was isolated as an aroma precursor from tea leaves (Camellia sinensis var. sinensis cv Shuixian) for oolong tea. The isolation was guided by a two-phase acid hydrolysis and/or an enzymatic hydrolysis followed by GC and GC-MS analyses.

  摘要 从乌龙茶茶叶（Camellia sinensis var. sinensis cv Shuxian）中分离出一种新的香叶苷，香叶基6-O-β-d-吡喃木糖基-β-d-吡喃葡萄糖苷作为香气前体。分离由两相酸水解和/或酶水解指导，然后进行 GC 和 GC-MS 分析。
• Efficient Synthesis of β‐Primeverosides as Aroma Precursors by Transglycosylation of β‐Diglycosidase from <i>Penicillium multicolor</i>
  作者：Kazutaka Tsuruhami、Shigeharu Mori、Kanzo Sakata、Satoshi Amarume、Shigetaka Saruwatari、Takeomi Murata、Taichi Usui

  DOI：10.1080/07328300500439413

  日期：2005.11.1

  The enzyme activity transferring a beta-primeverosyl unit was found from culture filtrates of Penicillium multicolor IAM7153 and was useful for synthesizing a series of beta-primeverosides via a beta-primeverosyl transfer reaction in an aqueous-organic biphasic system. With the acceptors benzyl alcohol, 2-phenylethanol, and ( Z )-3-hexenol, the enzyme induced the transfer products benzyl, 2-phenylethyl, and ( Z )-3-hexyl beta-primeverosides in high yields of 51% to 70% based on the donor added. When geraniol and eugenol were used as acceptors, the corresponding geranyl and eugenyl beta-primeverosides were obtained in lower yields of 8% to 12%. The enzyme was an excellent tool for producing naturally occurring beta-primeverosides on a mmol scale.
• The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves
  作者：Sachiko Matsumura、Shunya Takahashi、Mariko Nishikitani、Kikue Kubota、Akio Kobayashi

  DOI：10.1021/jf960852b

  日期：1997.7.1

  Two general synthetic routes were established in order to synthesize two diglycosides, primeverosides (1) and vicianosides (2), found in tea leaves. Procedure 1 is based on the Koenig-Knorr type of condensation of aglycon alcohols and 1-alpha-bromohexabenzoylprimeverose (6) and is suitable for the condensation of primary alcohols. Procedure 2 is to combine tribenzoyl-beta-D-glucoside (8) and 1-alpha-bromotribenzoylxylose (4). The primeveroside of a tertiary alcohol was synthesized by this method which is also applicable to the synthesis of vicianosides. The hydrolysis rate of each of the 12 synthesized glycosides by a crude tea enzyme was evaluated, which suggest that the main glycosidase is primeverosidase and the enzyme mixture shows substrate specificity to both the carbohydrate and aglycon moieties.
• Guo, Wenfei; Yamauchi, Kazuyo; Watanabe, Naoharu, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 5, p. 962 - 964
  作者：Guo, Wenfei、Yamauchi, Kazuyo、Watanabe, Naoharu、Usui, Taiichi、Luo, Shaojun、Sakata, Kanzo

  DOI：——

  日期：——