(3R,4R,4aR,10bS)-3,4-diacetoxy-2-acetoxymethyltetrahydropyrano<5,6-c>-3,4-dihydroisocoumarin | 79581-39-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R,4aR,10bS)-3,4-diacetoxy-2-acetoxymethyltetrahydropyrano<5,6-c>-3,4-dihydroisocoumarin
• 英文别名: (2R,3R,4R,4aS,10bS)-3,4-Diacetoxy-2-acetoxymethyltetrahydropyrano<5,6-c>dihydroisocoumarin；tri-O-methylnorbergenin；(4aS)-3t,4c-diacetoxy-2c-acetoxymethyl-8,9,10-trimethoxy-(4ar,10bt)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one；(4aS)-3t,4c-Diacetoxy-2c-acetoxymethyl-8,9,10-trimethoxy-(4ar,10bt)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-on；Bergenin-di-O-methylether-triacetat；[(2R,3R,4R,4aS,10bS)-3,4-diacetyloxy-8,9,10-trimethoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl acetate
• CAS: 79581-39-8
• 化学式: C₂₂H₂₆O₁₂
• 分子量: 482.441
• InChiKey: YPCKAZHIIGYRBR-ODJUOBDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1,2,3-Trimethoxy-5-methoxycarbonyl-6-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (3R,4R,4aR,10bS)-3,4-diacetoxy-2-acetoxymethyltetrahydropyrano<5,6-c>-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Synthesis of bergenin-type C-glucosylarenes

  摘要：

  Reaction of 1,2,3-trimethoxybenzene with 2,3,4,6-tetra-O-benzyl-beta-d-glucopyranosyl trifluoroacetate (5) in the presence of BF3.OEt2 afforded the 4-beta-C-glycosylarene 6. Hydrogenolysis of 6, then O-methoxycarbonylation, and bromination gave 1-bromo-2,3,4-trimethoxy-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-d-glucopyranosyl)benzene (9). Bromine/lithium exchange of 9 and then reaction with diphenyl disulfide furnished 2,3,4-trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-D-glucopyranosyl)benzene (14), oxidation of which afforded the phenylsulfinyl derivative 15. Ortho-lithiaton of 15 and then reaction with methyl chloroformate gave 2,3,4-trimethoxy-6-methoxycarbonyl-1-phenylsulfinyl-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-D-glucop? yranosyl)benzene (17). Removal of the phenylsulfinyl group from 15 with Raney nickel and then lactonisation with sodium methoxide provided 8,10-di-O-methylbergenin (2). The 3,4,11-triacette (4) of 2 had physical data that accorded with those for the natural compound.

  DOI：

  10.1016/0008-6215(91)80148-g

文献信息

• C-glucosylarenes from O-α-d-glucosyl trichloroacetimidates. Structure of bergenin derivatives
  作者：Richard R. Schmidt、Gunther Effenberger

  DOI：10.1016/s0008-6215(00)90879-6

  日期：1987.12

  with an additional C -alkyl substituent. Introduction of an electron-withdrawing, C -acetyl substituent into the phloroglucinol structure lowered the reactivity. The reaction could be extended to 1,2,3- and 1,2,4-trioxysubstituted benzene derivatives to give the bergenin derivative (3 R ,4 R ,4a R ,10b S )-3,4-diacetoxy-2-acetoxymethyltetrahydropyrano[5,6- C ]-3,4-dihydroisocoumarin via an intramolecular

  摘要用O-α-d-吡喃葡萄糖基三氯乙亚胺酸酯对氧取代的苯衍生物进行C-葡萄糖基化反应，主要生成β-d-吡喃葡萄糖基芳烃。最有效的催化剂是乙醚·三氟化硼，乙醚·氯化锌和氯化锌。用完全和部分O-保护的间苯三酚成功进行了反应，并且它还与另外的C-烷基取代基相容。将吸电子的C-乙酰基取代基引入间苯三酚结构降低了反应性。该反应可扩展至1,2,3-和1,2,4-三氧基取代的苯衍生物，以得到伯来宁衍生物（3 R，4 R，4a R，10b S）-3,4-二乙酰氧基-2-乙酰氧基甲基四氢吡喃[5,6-C] -3,4-二氢异香豆素通过该反应的分子内形式。O-保护的间苯二酚和二氧基取代的苯的C-取代的衍生物得到各种4-C-葡糖基-苯和苯并二氢吡喃。从9-三甲基甲硅烷基氧基蒽（作为一元氧基取代的苯衍生物）获得蒽酮的C-葡糖基衍生物的端基异构体混合物。由O-酰化的三氯乙酰亚氨酸酯合成纯的β-d异构体。
• Sur la constitution de la bergénine
  作者：Th. Posternak、K. Dürr

  DOI：10.1002/hlca.19580410424

  日期：——

  La bergénine représente la δ-lactone (V) d'un acide aldohexo-pyranosyl-2-(O-méthyl)-4-gallique.

  Labergéninereprésentelaδ-内酯（V）d'un acide aldohexo-pyranosyl-2-（O-méthyl）-4-gallique。
• Synthesis of bergenin-related natural products by way of an intramolecular C-glycosylation reaction
  作者：Cyril Rousseau、Olivier R Martin

  DOI：10.1016/s0957-4166(99)00484-x

  日期：2000.2

  The peracetate of tri-O-methylnorbergenin 16 as well as the cis-fused epimer of 16, which constitutes the core C-aryl glycosidic fragment of castacrenin B, were prepared by way of the IDCP-mediated intramolecular C-arylation of a pentenyl beta-D-glucopyranoside carrying, at O-2, a 3,4,5-trimethoxybenzyl substituent. (C) 2000 Elsevier Science Ltd, All rights reserved.