2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->6)-1,2,3,4-tera-O-benzoyl-β-D-glucopyranose | 192827-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->6)-1,2,3,4-tera-O-benzoyl-β-D-glucopyranose
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Xyl(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(b)-O-Bz；[(3R,4S,5R,6R)-4,5-dibenzoyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrabenzoyloxyoxan-2-yl]methoxy]oxan-3-yl] benzoate
• CAS: 192827-10-4
• 化学式: C₆₀H₄₈O₁₇
• 分子量: 1041.03
• InChiKey: RFIXVGKAHPGSCI-IWIYKOIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  77
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->6)-1,2,3,4-tera-O-benzoyl-β-D-glucopyranose 在 sodium methylate 、 氰化汞 、 溴化钛(IV) 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 19.0h， 生成 (2R,3R,4S,5S,6R)-2-(苯基甲氧基)-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：

  The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves

  摘要：

  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.

  DOI：

  10.1021/jf960852b
• 作为产物：
  描述：

  1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose 、 2,3,4-tri-O-benzoyl-α-D-xylopyranosyl bromide 在 氰化汞 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->6)-1,2,3,4-tera-O-benzoyl-β-D-glucopyranose
  参考文献：
  名称：

  The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves

  摘要：

  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.

  DOI：

  10.1021/jf960852b

文献信息

• First total synthesis of two new diglycosides, neohancosides A and B, from Cynanchum hancockianum
  作者：Yaeko Konda、Tsuneyuki Toida、Eisuke Kaji、Kazuyoshi Takeda、Yoshihiro Harigaya

  DOI：10.1016/s0008-6215(97)00086-4

  日期：1997.6

  Abstract Neohancosides A (1) and B (2) are monoterpene diglycosides isolated from Cynanchum hancockianum , which is a Chinese folk medicine having antitumor activity. First total synthesis of 1 and 2 , (3 R )-linaloyl and (3 R )-8-hydroxylinaloyl 3- O - β -d-xylopyranosyl-(1 → 6)-β-d-glucopyranosides were achieved stereoselectively using fluoride 12b as a glycosyl donor. The asymmetry of C-3 in 1 and

  摘要新汉果苷A（1）和B（2）是从汉防草中分离出的单萜二糖苷，这是一种具有抗肿瘤活性的中草药。使用氟化物12b立体选择性地完成1和2的第一个全合成，（3 R）-芳基酰基和（3 R）-8-羟基芳基酰基3-O-β-d-吡喃吡喃糖基-（1→6）-β-d-吡喃吡喃糖苷。作为糖基供体。通过分离（3 R），（3 S）-芳酰基和（3 R），（3 S）-8-苯甲酰氧基芳醛基3-O -2,3， 4-三-O-苯甲酰基-β-d-吡喃葡萄糖苷，分别为19和21以及20和22。1和2的绝对构型由合成中间体33和34的酶促降解确定。