2,3:4,5-di-O-isopropylidene-(+)-epi-quercitol | 229612-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:4,5-di-O-isopropylidene-(+)-epi-quercitol
• 英文别名: 1,2:3,4-di-O-isopropylidene-5S-(+)-proto-quercitol；(1S,2S,6S,7S,9R)-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol
• CAS: 229612-81-1
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: DMHGPKRSZAXQJK-SVSWQMSJSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  349.6±42.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3:4,5-di-O-isopropylidene-(+)-epi-quercitol 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 以78%的产率得到(3aα,4α,5β,7β,7aα)-hexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4,5,7-triol
  参考文献：
  名称：

  从（+）-表-和（-）-维生素-槲皮醇方便地合成3-和6-脱氧-D-肌醇磷酸酯类似物。

  摘要：

  从通过肌醇生物转化而容易产生的（+）-表-和（-）-维-槲皮醇开始，一些生物学上有趣的磷酸盐和多磷酸盐类似物，包括3的Ins（1,4,5）P（3）衍生物-脱氧-和6-脱氧-D-肌醇可以容易地以常规方式制备。此外，3-脱氧Ins（1,4,5）P（3）在C-2处的化学修饰提供了2-电子异构体，2-脱氧和2-脱氧-2-氟形式。测定了获得的八种多磷酸盐类似物对PDH-Pase和PDH-K以及G6Pase的生物学活性，但没有一个被证明是阳性的。

  DOI：

  10.1016/j.bmcl.2006.06.096
• 作为产物：
  描述：

  原栎醇 在 lithium aluminium tetrahydride 、 乙酸酐 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2,3:4,5-di-O-isopropylidene-(+)-epi-quercitol
  参考文献：
  名称：

  伏格列波糖启发的新型强力α-葡萄糖苷酶抑制剂N-1,3-二羟丙基氨基环糖醇的合成

  摘要：

  伏格列波糖（一种N-1,3-二羟丙基氨基环糖醇）已广泛用作糖尿病治疗的有效α-葡萄糖苷酶抑制剂。已经进行了多种尝试，以通过各种氨基环糖醇和丙烷-1，3-二醇的偶联来合成紧密相关的类似物。然而，它们大多数显示出较弱的抑制作用或没有抑制作用。在这次交流中，我们使用（+）-原-槲皮醇（1）作为环糖醇核心结构合成了一对新的N-1,3-二羟丙基氨基环糖醇（10和11）。新合成的化合物显示出强效的大鼠肠道α-葡萄糖苷酶，尤其是针对麦芽糖酶的酶，其IC50值为亚微摩尔。随后对11抑制作用机理的研究表明了对麦芽糖酶和蔗糖酶的竞争方式。通过对接研究详细阐述了这些化合物的有效抑制作用，其中它们与活性位点中关键氨基酸残基的结合曲线与伏格列波糖相似。因此，将丙烷-1,3-二醇部分引入合适的环己烷核心结构（如氨基槲皮醇）将是发现一系列新的有效α-葡萄糖苷酶抑制剂的潜在途径。

  DOI：

  10.1016/j.carres.2016.04.014

文献信息

• (+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols
  作者：Sumrit Wacharasindhu、Wisuttaya Worawalai、Wimolpun Rungprom、Preecha Phuwapraisirisan

  DOI：10.1016/j.tetlet.2009.02.153

  日期：2009.5

  diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protection of the hydroxy group which was further functionalized into the target aminocyclitol in a straightforward manner. The present approach provides a protocol for preparing aminocyclitols

  描述了由天然可得的（+）-原-槲皮醇（1）有效合成非对映体纯的5-氨基-1,2,3,4-环己烷四醇（6和11）和槲皮醇衍生物。立体化学1的建立是为了对羟基进行区域选择性保护，该羟基以直接的方式进一步官能化成目标氨基环糖醇。本方法提供了用于大量制备氨基环醇的方案。另外，使用改进的Mosher方法解决了（+）-原-槲皮醇的绝对立体化学。在合成的氨基环糖醇中，有11种可能通过IC抑制α-葡萄糖苷酶50值12.5μM，其比标准降糖药，阿卡波糖的大45倍的®。
• Quercitylcinnamates, a new series of antidiabetic bioconjugates possessing α-glucosidase inhibition and antioxidant
  作者：Eakkaphon Rattanangkool、Preecha Kittikhunnatham、Thanakorn Damsud、Sumrit Wacharasindhu、Preecha Phuwapraisirisan

  DOI：10.1016/j.ejmech.2013.05.047

  日期：2013.8

  Antidiabetic agents possessing dual functions, alpha-glucosidase inhibition and antioxidant, have been accepted to be more useful than currently used antidiabetic drugs because they not only suppress hyperglycemia but also prevent risk of complications. Herein, we design antidiabetic bioconjugates comprising of (+)-proto-quercitol as a glucomimic and cinnamic analogs as antioxidant moieties. Fifteen quercitylcinnamates were synthesized by direct coupling through ester bond in the presence of DCC and DMAP. Particular quercityl esters 6a, 7a and 8a selectively inhibited rat intestinal maltase and sucrose 4 -6 times more potently than their parents 6, 7 and 8. Of synthesized bioconjugates, 6a was the most potent inhibitor against maltase and sucrose with IC50 values of 531 and 43.65 mu M, respectively. Of interest, its inhibitory potency toward maltase was 6 times greater than its parent, caffeic acid (6), while its radical scavenging (SC50 0.11 mM) was comparable to that of commercial antioxidant BHA. Subsequent investigation on mechanism underlying inhibitory effect of 6a indicated that it blocked maltase and sucrose functions by mixed inhibition through competitive and noncompetitive manners. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Amine-linked diquercitols as new α-glucosidase inhibitors
  作者：Wisuttaya Worawalai、Sumrit Wacharasindhu、Preecha Phuwapraisirisan

  DOI：10.1016/j.bmcl.2014.09.064

  日期：2014.12

  Two new diastereomeric amine-linked diquercitols 7 and 8 were synthesized by reductive amination of ketoquercitol 4 and epimeric aminoquercitols 3 and 6. The ketone and amines were successfully prepared, without the formation of byproducts, from naturally available (+)-proto-quercitol (1). The amine-linked diquercitols showed inhibitory effect against alpha-glucosidases with more pronounced potency than their original aminoquercitol monomers. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of glucocerebrosidase inhibitory activity of anhydro deoxyinositols from (+)-epi-and(−)-vibo-quercitols
  作者：Seiichiro Ogawa、Satoko Uetsuki、Yoji Tezuka、Takayuki Morikawa、Atsushi Takahashi、Kiyoshi Sato

  DOI：10.1016/s0960-894x(99)00223-1

  日期：1999.6

  Twelve 1,2- and 2,3-anhydro-1,2,3,4,5-cyclohexanepentols were synthesized from (+)-epi- and (-)-vibo-quercitols, readily available by bioconversion of myo-inositol, and assayed for inhibitory activity against glucocerebrosidase (mouse liver). Among them 1L-1,2-anhydro-1,2,4/3,5-cyclohexanepentol, the 3-deoxy derivative of the irreversible inhibitor conduritol B epoxide (CBE), has been demonstrated to be a highly potent and specific inhibitor, almost comparable to the parent compound. (C) 1999 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1
  作者：Seiichiro Ogawa、Hiroshi Aoyama、Yoji Tezuka

  DOI：10.1081/car-100108284

  日期：——

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.