tert-butyl {(4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}carbamate | 870279-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl {(4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}carbamate
• 英文别名: tert-butyl N-[[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 870279-45-1
• 化学式: C₁₂H₂₃NO₅
• 分子量: 261.318
• InChiKey: PKQUWGIDQDCBPD-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl {(4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}carbamate 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -30.0~20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786
• 作为产物：
  描述：

  methyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid-5-carboxylate 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 三乙基硼 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 lead(IV) tetraacetate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.42h， 生成 tert-butyl {(4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}carbamate
  参考文献：
  名称：

  的立体选择性施工抗-和顺式经由α-烷氧基酰基碲化物的decarbonylative自由基偶合-1,2-二醇结构

  摘要：

  衍生自d-酒石酸的α-烷氧基酰基碲化物用于具有电子缺陷双键的立体选择性偶联反应。在室温下用Et 3 B / O 2或Et 3 B / O 2 / HSi（SiMe 3）3处理α-烷氧基酰基碲化物可促进酰基的形成并随后脱羰形成相应的α-烷氧基，将其添加到与吸电子基团共轭的各种C C和C N键。立体化学结果由酒石酸衍生物的保护基团定义：丙酮化物和2,3-二甲氧基丁烷-2,3-二氧基乙缩醛控制抗-和SYN -stereoselectivities，分别。

  DOI：

  10.1016/j.tet.2016.06.056

文献信息

• Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics
  作者：Keith Clinch、Gary B. Evans、Richard F.G. Fröhlich、Shivali A. Gulab、Jemy A. Gutierrez、Jennifer M. Mason、Vern L. Schramm、Peter C. Tyler、Anthony D. Woolhouse

  DOI：10.1016/j.bmc.2012.07.006

  日期：2012.9

  Several acyclic hydroxy-methylthio-amines with 3-5 carbon atoms were prepared and coupled via a methylene link to 9-deazaadenine. The products were tested for inhibition against human MTAP and Escherichia coli and Neisseria meningitidis MTANs and gave K-i values as low as 0.23 nM. These results were compared to those obtained with 1st and 2nd generation inhibitors (1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol (MT-Immucillin-A, 3) and (3R,4S)-1-[9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine (MT-DADMe-Immucillin-A, 4). The best inhibitors were found to exhibit binding affinities of approximately 2- to 4-fold those of 3 but were significantly weaker than 4. Cleavage of the 2,3 carbon-carbon bond in MT-Immucillin-A (3) gave an acyclic product (79) with a 21,500 fold loss of activity against E. coli MTAN. In another case, N-methylation of a side chain secondary amine resulted in a 250-fold loss of activity against the same enzyme [(+/-)-65 vs (+/-)-68]. The inhibition results were also contrasted with those acyclic derivatives previously prepared as inhibitors for a related enzyme, purine nucleoside phosphorylase (PNP), where some inhibitors in the latter case were found to be more potent than their cyclic counterparts. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase
  作者：Joel R. Walker、C. Dale Poulter

  DOI：10.1021/jo0516786

  日期：2005.11.1

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.
• Stereoselective construction of anti - and syn -1,2-diol structures via decarbonylative radical coupling of α-alkoxyacyl tellurides
  作者：Shoko Matsumura、Yuki Matsui、Masanori Nagatomo、Masayuki Inoue

  DOI：10.1016/j.tet.2016.06.056

  日期：2016.8

  α-Alkoxyacyl tellurides derived from d-tartaric acid were utilized for stereoselective coupling reactions with electron-deficient double bonds. Treatment of the α-alkoxyacyl tellurides with Et3B/O2 or Et3B/O2/HSi(SiMe3)3 at room temperature promoted acyl radical formation and subsequent decarbonylation to form the corresponding α-alkoxy radicals, which added to various CC and CN bonds conjugated with

  衍生自d-酒石酸的α-烷氧基酰基碲化物用于具有电子缺陷双键的立体选择性偶联反应。在室温下用Et 3 B / O 2或Et 3 B / O 2 / HSi（SiMe 3）3处理α-烷氧基酰基碲化物可促进酰基的形成并随后脱羰形成相应的α-烷氧基，将其添加到与吸电子基团共轭的各种C C和C N键。立体化学结果由酒石酸衍生物的保护基团定义：丙酮化物和2,3-二甲氧基丁烷-2,3-二氧基乙缩醛控制抗-和SYN -stereoselectivities，分别。