(S)-4-(Benzyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane | 176094-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-(Benzyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane
• 英文别名: 4-benzyloxymethyl-2,2-dioxo-1,3,2-dioxathiolane；4-(Phenylmethoxymethyl)-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 176094-54-5
• 化学式: C₁₀H₁₂O₅S
• 分子量: 244.268
• InChiKey: HGNFAVXSHSUMLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-(Benzyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane 在 sodium hydride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 68.33h， 生成 (+)-(1S,2R)-2-(benzyloxymethyl)-1-(ethoxycarbonyl)cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine

  摘要：

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.

  DOI：

  10.1021/jo00087a039
• 作为产物：
  描述：

  4-(benzyloxymethyl)-1,3-dioxo-2-thiolane 2-oxide 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 、 乙腈 、 Petroleum ether 为溶剂， 反应 24.0h， 生成 (S)-4-(Benzyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane
  参考文献：
  名称：

  Synthesis of 1,1-Dibromo-3-hydroxyalkanes via Opening of Cyclic Sulfates

  摘要：

  3-烷氧基-1,1-二溴烷是用于二氨基酸选择性溴锂交换反应的有趣底物。本文通过二溴甲基锂与1,2-二醇的环硫酸酯反应，描述了一种制备前体1,1-二溴-3-羟基烷的通用路线。

  DOI：

  10.1055/s-1996-4193

文献信息

• Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp³)–C(sp³) Kumada-Type Coupling of Cyclic Sulfate Esters
  作者：Rodrigo Ramírez-Contreras、Bill Morandi

  DOI：10.1021/acs.orglett.6b01745

  日期：2016.8.5

  This contribution describes a copper-catalyzed, C(sp3)–C(sp3) cross-coupling reaction of cyclic sulfate esters, a distinct class of electrophilic derivatives of polyols, with alkyl Grignard reagents to afford functionalized alcohol products in good yields. The method is operationally simple and highlights the potential of cyclic sulfate esters as highly reactive substrates in catalytic, chemoselective

  该贡献描述了铜硫酸酯，环状硫酸酯（多元醇的独特亲电衍生物）与烷基格氏试剂的铜催化C（sp 3）-C（sp 3）交叉偶联反应，可提供高收率的官能化醇产品。该方法操作简单，突出了环硫酸酯作为催化，化学选择性多元醇转化中高反应性底物的潜力。
• Novel succinate derivative compounds useful as cysteine protease inhibitors
  申请人：——

  公开号：US20010041700A1

  公开（公告）日：2001-11-15

  Disclosed are novel succinate derivative compounds of the formula (I)/(Ia): 1 wherein R1, R2, R3, R4, R5, R6, R7, X and A are defined herein. The compounds are useful as inhibitors of cysteine proteases. Also disclosed are methods of using and methods of making such compounds.

  披露了新型琥珀酸衍生物化合物，其化学公式为(I)/(Ia)：1，其中R1、R2、R3、R4、R5、R6、R7、X和A的定义如下。这些化合物可用作胱氨酸蛋白酶的抑制剂。还披露了使用和制造这些化合物的方法。
• Efficient Synthesis of Fluorophosphonylated Alkyles by Ring-Opening Reaction of Cyclic Sulfates
  作者：Sonia Amel Diab、Aboubacary Sene、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/ol801443s

  日期：2008.9.1

  Ring-opening reactions of functionalized 1,2-cyclic sulfates and oxetanes with the phosphonodifluoromethyl carbanion are reported. This approach allows an easy access to fluorinated beta-hydroxyphosphonates that are building blocks in the synthesis of acyclic nucleosides. Synthesis of precursors of nucleoside phosphorylase inhibitors from these alcohols is described.

  据报道官能化的1，2-环硫酸盐和氧杂环丁烷与膦酰基二氟甲基碳负离子的开环反应。这种方法可以轻松获得氟化的β-羟基膦酸酯，后者是无环核苷合成中的基础。描述了由这些醇合成核苷磷酸化酶抑制剂的前体。
• One-Pot Three-Component Click Reaction of Cyclic Sulfates and Cyclic Sulfamidates
  作者：Alicia Megia-Fernandez、Mariano Ortega-Muñoz、Fernando Hernandez-Mateo、Francisco Santoyo-Gonzalez

  DOI：10.1002/adsc.201100813

  日期：2012.6.18

  copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) of cyclic sulfates or cyclic sulfamidates in the presence of sodium azides and alkynes is reported. The developed protocol takes also advantage of the concomitant use of microwave (MW) irradiation and heterogeneous catalysis. The protocol allows the fast and efficient preparation of (alkyl sulfate)‐ and (alkyl sulfamidate)‐1H‐1,2,3‐triazoles in a simple

  报道了一种在叠氮化钠和炔烃存在的情况下涉及串联叠氮化和单击铜（I）催化的环状硫酸盐或环状氨基磺酸盐的叠氮化物-炔烃环加成（CuAAC）的单锅，三组分方法。所开发的协议还利用了微波（MW）辐照和非均相催化的同时使用。该方案允许以简单的方式快速有效地制备（烷基硫酸盐）-和（氨基磺酸烷基酯）-1 H -1,2,3-三唑。
• A convenient synthesis of 1-(diethoxyphosphoryl)cyclopropanecarboxylates
  作者：Henryk Krawczyk、Katarzyna Wąsek、Jacek Kędzia、Jakub Wojciechowski、Wojciech M Wolf

  DOI：10.3998/ark.5550190.0011.913

  日期：——

  An efficient synthesis of a series of 1-(diethoxyphosphoryl)cyclopropancarboxylates was accomplished by the reaction of terminal 1,2-diols cyclic sulfates with triethylphosphonoacetate. The stereochemistry of 2-benzyloxymethyl-1-(diethoxyphosphoryl)cyclopropanecarboxylic acid was determined by the single crystal X-ray structure analysis.

  通过末端 1,2-二醇环状硫酸盐与三乙基膦酰基乙酸酯的反应，实现了一系列 1-（二乙氧基磷酰基）环丙烷羧酸酯的有效合成。2-苄氧基甲基-1-(二乙氧基磷酰基)环丙烷羧酸的立体化学通过单晶X射线结构分析确定。