3-O-pivaloyl morphine | 150631-28-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 3-O-pivaloyl morphine
• 英文别名: 3-pivaloyl morphine；3-o-Pivaloylmorphine；[(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] 2,2-dimethylpropanoate
• CAS: 150631-28-0
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: FLMPSAHAQDPFJX-XHXBRUBBSA-N

物化性质

• 沸点：
  513.4±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-pivaloyl morphine 在 吡啶 、 三氧化硫吡啶 作用下， 生成 M3P6S
  参考文献：
  名称：

  Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners

  摘要：

  A series of 3-O-acyl-6-O-sulfate esters of morphine, dihydromorphine, N-methylmorphinium iodide, codeine, and dihydrocodeine were prepared and evaluated for their ability to bind to mu-, delta-, kappa(1)-, kappa(2)-, and kappa(3)-opiate receptors. Several compounds exhibited good affinity for the p-opiate receptor. Morphine-3-O-propionyl-6-O-sulfate had four times greater affinity than morphine at the mu-opiate receptor and was the most selective compound at this receptor subtype. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.060
• 作为产物：
  描述：

  三甲基乙酰氯 、 吗啡 生成 3-O-pivaloyl morphine
  参考文献：
  名称：

  Structure–activity relationships of some opiate glycosides

  摘要：

  A number of analogues of morphine-6-glucuronide 1 have been prepared and evaluated as potential analgesic agents by competitive mu-receptor binding assay and in vivo antinociceptive activity. The analogues show variation in the nature of the carbohydrate residue, the N-substituent, the O(3)-substituent and saturation of the 7,8-double bond compared to 1. In general, only the 6beta-glucoside or beta-glucuronide carbohydrate residues showed potent agonism; other modified carbohydrates were less active or exhibited potential antagonism. Variations in N-substituent led to either reduced agonism (N-H) or potential antagonism [N-allyl, N-(cyclopropyl)methyl]; a polar N-substituent, carboxymethyl, failed to bind. Saturation of the 7,8-double bond led to increased agonism compared to the parent compound in all three examples studied. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00056-8
• 作为试剂：
  描述：

  、 3-O-pivaloyl morphine 在 3-O-pivaloyl morphine 作用下， 以29的产率得到
  参考文献：
  名称：

  Chem. Pharm. Bull. 1968, 16, 2114-2119

  摘要：

  DOI：

文献信息

• Preparation, X-ray structure and reactivity of a stable glycosyl iodide
  作者：Jamie Bickley、Jennifer A. Cottrell、John R. Ferguson、Robert A. Field、John R. Harding、David L. Hughes、K. P. Ravindanathan Kartha、Jayne L. Law、Feodor Scheinmann、Andrew V. Stachulski

  DOI：10.1039/b302629a

  日期：——

  Highly selective reaction of methyl tetra-O-pivaloyl-β-D-glucopyranuronate 2 with iodotrimethylsilane or (Me3Si)2 and I2 affords, in excellent yield, the ‘disarmed’ glycosyl iodide 1 which has good stability at 20 °C and excellent stability at 0 °C; the X-ray crystal structure of 1 is described, along with a comparison of its utility as a glycosyl donor to that of the corresponding bromide.

  甲基四-O-叔丁酰基-β-D-吡喃葡萄糖苷酸2与碘三甲基硅烷或(Me3Si)2和I2发生高选择性反应，以优异的产率生成“解除武装”的糖基碘化物1，其在20°C下具有良好的稳定性，0°C下稳定性极佳；描述了1的X射线晶体结构，并将其作为糖基供体的效用与相应溴化物的效用进行了比较。
• MORPHINE-6-GLUCURONIDE SYNTHESIS
  申请人：Cenes Limited

  公开号：US20030083476A1

  公开（公告）日：2003-05-01

  The invention provides a novel method for synthesising M6G, and intermediates therefor. In order to synthesise M6G the major problem to overcome is to obtain the glycoside linkage with very high &bgr;-selectivity since prior methods produce the &agr;-anomer. The invention provides a method for the preferential synthesis of the &bgr;-anomer of M6G which includes the step shown in Scheme 6 wherein use of DMAP is optional.

  这项发明提供了一种合成M6G及其中间体的新方法。为了合成M6G，需要克服的主要问题是获得具有非常高β-选择性的糖苷键，因为先前的方法会产生α-异构体。该发明提供了一种优先合成M6G的β-异构体的方法，其中包括方案6中所示的步骤，其中使用DMAP是可选的。
• Morphine-6-glucuronide synthesis
  申请人：Genes Limited

  公开号：US06566510B1

  公开（公告）日：2003-05-20

  The invention provides a novel method for synthesizing Morphine-6-Glucuronide comprising the step of reacting 3-O-pivaloyloxymorphine and methyl 1&agr;,2-ethylorthopivalate-3-4,di-O-pivaloylglucouronate.

  本发明提供了一种合成吗啡-6-葡萄糖醇的新方法，包括反应3-O-戊酰氧基吗啡和甲基1&agr;，2-乙基正戊酸酯-3-4，二戊酰基葡萄糖酸酯。
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• WO9964430A2
  申请人：——

  公开号：——

  公开（公告）日：——