((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester | 324535-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3aS,4R,6S,6aR)-4-hydroxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]carbamate
• CAS: 324535-77-5
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: KYERKABTFXCUKM-JLIMGVALSA-N

物化性质

• 沸点：
  404.8±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  ((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester 在 盐酸 、 sodium periodate 、 Jones reagent 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 异丙醇 、 丙酮 为溶剂， 反应 100.92h， 生成 (+)-lycoperdic acid
  参考文献：
  名称：

  合成番茄红酸的两种对映异构体，这是一种不寻常的蘑菇衍生氨基酸。

  摘要：

  用手性氨基醇有效合成了番茄红素酸的两种对映体，番茄红素是一种来自食用蘑菇 Lycoperdon perlatum 的 4-羟基谷氨酸衍生物。关键步骤是将 C3 单元立体选择性地引入双环酮和将环状邻二醇氧化裂解为二羧酸。该报告提供了 (-)-番茄红酸的首次合成。

  DOI：

  10.1093/bbb/zbaa027
• 作为产物：
  描述：

  (1S,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-cyclopent-2-enol 在 lithium hydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 对甲苯磺酸 、 巯基乙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 138.0h， 生成 ((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q

  摘要：

  A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.043

文献信息

• Rapid syntheses of either enantiomer of important carbocyclic nucleoside precursors
  作者：Brock T Shireman、Marvin J Miller

  DOI：10.1016/s0040-4039(00)01668-3

  日期：2000.12

  The syntheses of both enantiomers of aminocyclopentanetriol 1, a versatile carbocyclic nucleoside precursor, is reported utilizing an amino acid-derived acylnitroso Diels–Alder cycloaddition. The sequence is practical and proceeds in an overall yield of 36% from the d-alanine-derived hydroxamic acid.

  据报道，利用氨基酸衍生的酰基亚硝基Diels-Alder环加成法，合成了一种通用的碳环核苷前体氨基环戊三醇1的两种对映体。该序列是实用的，并且从d-丙氨酸衍生的异羟肟酸的总产率为36％。
• Synthesis of Novel Carbocyclic Adenosine Analogues as Inhibitors of Adenosine Kinase
  作者：Marlon Cowart、Michael J. Bennett、James F. Kerwin

  DOI：10.1021/jo981658m

  日期：1999.4.1

  Several new 4'-amino substituted carbocyclic adenosine analogues (6, 7, 31) were prepared as potential inhibitors of the enzyme adenosine kinase. Three different heterocyclic base moieties (adenine, 8-azaadenine, and pyrazolo[3,4-d]pyrimidine) were incorporated into carbocyclic nucleoside analogues through the use of two different synthetic strategies. In both strategies, bicyclic isoxazolidine 9 (prepared through a hetero Diels-Alder reaction with cyclopentadiene) was used as the starting material. In one route, the N-O bond was reductively cleaved, and the hydroxyl group (after inversion and ring functionalization) was used as a leaving group to incorporate the heterocyclic base moiety as the key bond-forming step. A second, more efficient and higher yielding synthetic route was developed as a general solution to the synthesis of the target 4'-amino substituted carbocyclic adenosine analogues. In this methodology, the allylic C-O bond in the bicyclic isoxazolidine 9 was cleaved with double stereoinversion under palladium(0) catalysis as the key bond-forming step to stereospecifically incorporate the heterocyclic base moiety into the cyclopentane ring. The regioselectivity of key bond-forming steps was established principally by NMR methods, especially through (13)C NMR shifts and by NOE effects seen in the analogues, as well as by HMBC/HMQC experiments.
• An enantioselective synthesis of the cyclopentene fragment of nucleoside Q
  作者：Kyung-Hee Kim、Marvin J. Miller

  DOI：10.1016/s0040-4039(03)00973-0

  日期：2003.6

  An enantioselective synthesis of (3S,4R,5S)-(+)-3-amino-4.5-dihydroxycyclopentene, a segment of nucleoside Q and Q base. is reported utilizing an amino acid-derived acylnitroso Diels-Alder cycloaddition. (C) 2003 Elsevier Science Ltd. All rights reserved.