(R)-(2-oxo-1,3-oxazolidin-5-yl)methyl mesylate | 113420-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-(2-oxo-1,3-oxazolidin-5-yl)methyl mesylate
• 英文别名: (R)-5-(methanesulfonyloxymethyl)-2-oxazolidinone；(5R)-5-(methanesulfonyloxymethyl)oxazolidin-2-one；(R)-(2-oxooxoazolidine-5-yl)methyl methansulfonate；(R)-(2-oxoazolidin-5-yl)methylmethansulfonate；[(5R)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate
• CAS: 113420-86-3
• 化学式: C₅H₉NO₅S
• 分子量: 195.196
• InChiKey: VKAFSPRIQUAZHG-SCSAIBSYSA-N

物化性质

• 熔点：
  117.7 °C
• 沸点：
  535.9±19.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(2-oxo-1,3-oxazolidin-5-yl)methyl mesylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (R)-5-azidomethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS MEDICAMENTS

  摘要：

  该发明涉及公式1的新取代萘啉类化合物，以及其药理学上可接受的盐、对映体、旋光异构体、消旋体、水合物或溶剂合物，其中R1从—O—R3或—NR3R4中选择，R3是经R5和R6取代的C1-6烷基，R5从氢、支链或直链C1-6烷基、C2-6烯基、—C1-6烷基氧基-C1-3烷基、C1-3卤代烷基中选择，R6是环X，其中n为0或1，为单键或双键，A、B、D和E各自独立地从CH2、CH、C、N、NH、O或S中选择，环X通过位置A、B、D或E连接到分子，所述环X可以选择地进一步由氧代、羟基、—C1-3烷基、—C1-3卤代烷基、—O—C1-3烷基、—C1-3烷醇和卤素中的每个单独选择的一个、两个或三个残基取代，并且R4、R2、R7、R8、R9、R10、R11和Q可以具有如权利要求1中所给出的含义，以及含有这些化合物的药物组合物。

  公开号：

  US20120028939A1
• 作为产物：
  描述：

  [(5R)-3-tert-butyl-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate 在 三氟乙酸 作用下， 反应 4.0h， 以100%的产率得到(R)-(2-oxo-1,3-oxazolidin-5-yl)methyl mesylate
  参考文献：
  名称：

  [EN] BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
  [FR] COMPOSES HETEROCYCLIQUES BIFONCTIONNELS ET PROCEDES DE FABRICATION ET D'UTILISATION DE CES COMPOSES

  摘要：

  公开号：

  WO2004029066A3

文献信息

• NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME
  申请人：Ryono Denis E.

  公开号：US20080009465A1

  公开（公告）日：2008-01-10

  Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R 4 is —(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 ), —(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g , —(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g , —(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10 ), or —(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10 ); R 5 and R 6 are independently selected from H, alkyl and halogen; Y is R 7 (CH 2 ) s or is absent; and X, n, Z, m, R 4 , R 5 , R 6 , R 7 , and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

  提供了磷酸酯和磷酸酯激活剂，因此在治疗糖尿病和相关疾病方面非常有用，并具有以下结构： 其中 是杂环芳基环； R 4 为—(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 )、—(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g 、—(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g 、—(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10) 或—(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10) ； R 5 和R 6 分别选择自H、烷基和卤素； Y为R 7 (CH 2 ) s 或不存在；以及 X、n、Z、m、R 4 、R 5 、R 6 、R 7 和s如本文所定义；或其药用盐。 还提供了一种利用上述化合物治疗糖尿病和相关疾病的方法。
• [EN] SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS SYK KINASE INHIBITORS<br/>[FR] NAPHTYRIDINES SUBSTITUÉES ET LEUR UTILISATION COMME INHIBITEURS DE SYK KINASE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011092128A1

  公开（公告）日：2011-08-04

  The invention relates to new substituted naphthyridines of formula (1), as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein R1 is selected from among -O-R3 or -NR3R4, R3 is C1-6-alkyl which is substituted by R5 and R6 R5 is selected from hydrogen, branched or linear C1-6-alkyl, C2-6-alkenyl, -C1-6-alkylen-O-C1-3-alkyl, C1-3-haloalkyl, R6 is ring X wherein n is either 0 or 1, and Formula (I) is a either a single or a double bond and wherein A, B, D and E are each independently from one another selected from CH2, CH, C, N, NH, O or S and wherein ring X is attached to the molecule either via position A, B, D or E, wherein said ring X may optionally be further substituted by one, two or three residues each selected individually from the group consisting of -oxo, hydroxy, -C1-3-alkyl, -C1-3-haloalkyl, -O-C1-3-alkyl, -C1-3-alkanol and halogen, and wherein R4, R2, R7, R8, R9, R10, R11 and Q may have the meanings as given in claim 1, as well as pharmaceutical compositions containing these compounds.

  该发明涉及公式（1）的新取代萘啉衍生物，以及其药理学上可接受的盐、对映体、非对映体异构体、立体异构体、水合物或溶剂化合物，其中R1从-O-R3或-NR3R4中选择，R3是C1-6-烷基，其被R5和R6取代，R5从氢、支链或直链C1-6-烷基、C2-6-烯基、-C1-6-烷基-氧-C1-3-烷基、C1-3-卤代烷基中选择，R6是环X，其中n为0或1，公式（I）为单键或双键，其中A、B、D和E分别独立地从CH2、CH、C、N、NH、O或S中选择，环X通过位置A、B、D或E连接到分子上，其中所述环X可以选择性地进一步被一个、两个或三个残基取代，每个残基分别从-氧化物、羟基、-C1-3-烷基、-C1-3-卤代烷基、-O-C1-3-烷基、-C1-3-醇基和卤素组成的群中选择，R4、R2、R7、R8、R9、R10、R11和Q的含义可以如权利要求1中所述，以及含有这些化合物的药物组合物。
• Efficient pathways to (R)- and (S)-5-hydroxymethyl-2-oxazolidinone and some derivatives
  作者：Karsten Danielmeier、Eberhard Steckhan

  DOI：10.1016/0957-4166(95)00144-e

  日期：1995.5

  2-Oxazolidinones are a very interesting class of compounds due to their various pharmacological effects. Two new syntheses of enantiomerically pure (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been developed starting with D-mannitol, L-ascorbic acid and (R)- or (S)-malic acid. (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been used to synthesize some new homochiral 2-oxazolidinone derivatives

  2-恶唑烷酮由于其各种药理作用而成为一类非常有趣的化合物。从D-甘露醇，L-抗坏血酸和（R）-或（S）-苹果酸开始，已开发出两个对映体纯的（R）-和（S）-5-羟甲基-2-恶唑烷酮的新合成方法。（R）-和（S）-5-羟甲基-2-恶唑烷酮已用于合成一些新的手性2-恶唑烷酮衍生物。
• An efficient synthesis of (R)-(+)- and (S)-(-)-propranolol from resolved 5-idomethyloxazo-lidin-2-ones
  作者：Giuliana Cardillo、Mario Orena、Sergio Sandri、Claudia Tomasini

  DOI：10.1016/s0040-4020(01)81657-4

  日期：——

  5S,R)-3-(1'-phenyleth-l'-yl)-5-iodomethyloxazolidin-2-ones, , have been synthesized and easily resolved by silica gel chromatography. Each pure diastereomer has been then converted to (S)-(-)-propranolol and (R)-(+)-propranolol , respectively. An empirical correlation of configuration and 1H NMR chemical shift for alternate diastereomers has been devised and has proved to be applicable in assigning

  （1'S *，5S，R）-3-（1'-苯基乙-1'-基）-5- iodomethyloxazolidin -2-酮，，已被合成，并通过硅胶色谱法容易地得到解决。然后将每种纯的非对映异构体分别转化为（S）-（-）-普萘洛尔和（R）-（+）-普萘洛尔。已经设计了与非对映异构体的构型和1 H NMR化学位移的经验相关性，并已证明可用于分配5-取代的3-（1'-苯基乙基-1'-基）草氮杂环丁烷-2-酮的构型。
• Development of a Safe, Scalable Process for the Preparation of an Oxaisoxazolidinone
  作者：U. Santhosh、Yogesh M. Kshirsagar、K. Venkatesan、Debasis Hazra、Jnaneshwara Kindel、R. Sridharan、David Ennis、Garnet E. Howells、Marijan Stefinovic、Sulur G. Manjunatha、Sudhir Nambiar

  DOI：10.1021/op500063g

  日期：2014.12.19

  This report describes the development and scale up of the synthesis of oxaisoxazolidinone 1, a significant synthon in the synthesis of the MRSA development compound AZD5847. Studies were carried out to ensure a short-term, risk based preparation of 9 on a 5 L scale with a solid isolation procedure and a safe, long-term manufacturing process for both 1 and 9 through extensive hazards evaluation.