(2R)-2-O-β-D-glucopyranosyloxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one | 113565-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-O-β-D-glucopyranosyloxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: (2R)-2-hydroxy-4,7-dimethoxy-1,4(2H)-benzoxazin-3-one glucoside；(2R)-4,7-dimethoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4-benzoxazin-3-one
• CAS: 113565-33-6
• 化学式: C₁₆H₂₁NO₁₀
• 分子量: 387.343
• InChiKey: UOASSFRPBORTCT-FFNJBFJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-Β-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟化硼乙醚 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (2R)-2-O-β-D-glucopyranosyloxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  环状半缩醛的双非对映选择性糖苷化：从禾本科植物中合成1,4-苯并恶嗪酮缩醛糖苷GDIBOA和GDIMBOA

  摘要：

  在一个步骤中的双非对映选择性glucosidation过程引起自然（2 - [R）-2- β构型的6，并且对于第一次，7，苯并嗪乙缩醛糖苷从禾本科物种，则通过的反应所描述ø - （2- ，3,4,6-四ö乙酰基β -D-吡喃葡萄糖基）三氯乙酰亚胺酯3作为葡糖供体与2,4-二羟基-2- ħ -1,4-苯并恶嗪-3（4 H ^） -酮1或它的7-甲氧基衍生物2 在过量三氟化硼醚化物作为促进剂存在下，作为半缩醛葡糖基受体，不需要对葡糖苷中的环状异羟肟酸单元进行共价保护。

  DOI：

  10.1016/0040-4020(96)00577-7

文献信息

• Induction of HDMBOA-Glc accumulation and DIMBOA-Glc 4-O-methyltransferase by jasmonic acid in poaceous plants
  作者：Akira Oikawa、Atsushi Ishihara、Hajime Iwamura

  DOI：10.1016/s0031-9422(02)00225-x

  日期：2002.10

  Induction of the accumulation of 2-(2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one)-beta-D-glucopyranose (HDMBOA-Glc) by jasmonic acid (JA) was investigated in wheat, Job's tears (Coix lacryma-jobi), and rye. An increase in HDMBOA-Glc and a corresponding decrease in 2-(2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one)-beta-D-glucopyranose (DIMBOA-Glc) were found in wheat and Job's tears, whereas no such changes were observed in rye. The activity of S-adenosyl-L-methionine:DIMBOA-Glc 4-O-methyltransferase which catalyzes the conversion of DIMBOA-Glc to HDMBOA-Glc was detected in wheat leaves treated with 50 muM JA. The activity started to increase 3 h after treatment with JA, reached a maximum after 9 h, and then decreased gradually. This mode of induction was well correlated with that for the accumulation of HDMBOA-Glc, indicating the induction of enzyme activity was responsible for the accumulation of HDMBOA-Glc. The enzyme was purified from JA-treated wheat leaves by three steps of chromatography, resulting in 95-fold purification. The enzyme showed strict substrate specificity for DIMBOA-Glc with a K value of 0.12 mM. DIBOA-Glc was also accepted as substrate, but the K-m value was 10 times larger than that for DIMBOAGlc. The aglycones, DIMBOA and DIBOA, were not methylated by the enzyme. The K-m value for S-adenoSyl-L-methionine was 0.06 mM The optimum pH and temperature were 7.5 and 35 degreesC, respectively. The activity was slightly enhanced by the presence of I mM EDTA, while heavy metal ions at 5 mM completely inhibited the activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Double diastereoselective glucosidation of cyclic hemiacetals: Synthesis of the 1,4-benzoxazinone acetal glucosides GDIBOA and GDIMBOA from Gramineae
  作者：Michael Kluge、Dieter Sicker

  DOI：10.1016/0040-4020(96)00577-7

  日期：1996.7

  lucopyranosyl) trichloroacetimidate 3 as glucosyl donor with 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one 1 or its 7-methoxy derivative 2 as hemiacetalic glucosyl acceptors in the presence of excess borontrifluoride etherate as promoter without a need for a covalent protection of the cyclic hydroxamic acid unit in the aglucones.

  在一个步骤中的双非对映选择性glucosidation过程引起自然（2 - [R）-2- β构型的6，并且对于第一次，7，苯并嗪乙缩醛糖苷从禾本科物种，则通过的反应所描述ø - （2- ，3,4,6-四ö乙酰基β -D-吡喃葡萄糖基）三氯乙酰亚胺酯3作为葡糖供体与2,4-二羟基-2- ħ -1,4-苯并恶嗪-3（4 H ^） -酮1或它的7-甲氧基衍生物2 在过量三氟化硼醚化物作为促进剂存在下，作为半缩醛葡糖基受体，不需要对葡糖苷中的环状异羟肟酸单元进行共价保护。