(1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol | 135486-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol
• 英文别名: (3aS,4S,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 135486-55-4
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: HDSUEAIIUCFODT-XQHKEYJVSA-N

物化性质

• 沸点：
  370.5±27.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol 在 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (-)-β-D-carbocyclic-1'-(9H-hypoxanthin-9-yl)-2',3'-O-isopropylidene ribonucleoside
  参考文献：
  名称：

  Synthesis of Chiral Carbocyclic Ribonucleotides

  摘要：

  The carbocyclic analogs of CMP, UMP, GMP, IMP, and ribo-TMP, of the same absolute configuration as the naturally occurring beta-D-ribofuranose-based ribonucleoside monophosphates, have been synthesized. The synthetic route employed Mitsunobu coupling of the heterocycles, appropriately protected where necessary, with a differentially protected, chiral carbocyclic core.

  DOI：

  10.1080/07328319908044853
• 作为产物：
  描述：

  (-)-(2R,3R,4R)-2,3-dihydroxy-2,3-O-isopropylidene-4-hydroxymethylcyclopentan-1-one 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 作用下， 生成 (1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol
  参考文献：
  名称：

  阿奇霉素生物合成的研究：2α，3α-二羟基-4β-（羟甲基）环戊烷-1β-胺的中间证据

  摘要：

  的双重标记的形式给药d葡萄糖到的发酵肉汤链霉菌citricolor随后同位素捕集已提供证据为2α，3α二羟基4β-（羟甲基）环戊烷-1β胺的中间性7或8中的核苷类抗生素阿霉素的生物合成1。

  DOI：

  10.1039/c39910000740

文献信息

• Highly asymmetric enzymatic hydrolysis and transesterification of meso-biscacetoxymethyl)- and bis(hydroxymethyl)cyclopentane derivatives: an insight into the active site model of Rhizopus Delemar lipase
  作者：Masakazu Tanaka、Miki Yoshioka、Kiyoshi Sakai

  DOI：10.1016/s0957-4166(00)80143-3

  日期：1993.5

  % ee. In explanation of these high enantioselectivities of RDL, the simple box-type active site model of enzyme was tentatively proposed. On the other hand, PFL-catalysed transesterification of meso-bis-(hydroxymethyl) cyclopentane (6) afforded (+)-16 of >99 % ee. The obtained (+) and (−)-16 were converted into the natural carbocyclic nucleoside (−)-aristeromycin (25), respectively.

  德氏根霉的脂肪酶（RDL）的水解-催化的内消旋-1,3-二（乙酰氧基甲基）环戊烷衍生物（7，12）和荧光假单胞菌脂肪酶（PFL）的水解-催化7个，得到手性单乙酸酯（15，16）的> 99％ee。为了解释RDL的高对映选择性，尝试性地提出了简单的盒型酶活性位点模型。另一方面，PFL催化的内消旋-双-（羟甲基）环戊烷（6）酯交换反应得到的（+）- 16 ee> 99％。将获得的（+）和（-）- 16转化为天然碳环核苷（-）-阿霉素（25）。
• 2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties
  作者：Chong Liu、Qi Chen、John D. Gorden、Stewart W. Schneller

  DOI：10.1016/j.bmc.2015.07.039

  日期：2015.9

  direction, this paper reports the strategic placement of a fluorine atom at the C-2 and C-3 positions and a methyl at the C-3 site of the 3-deazaadenine ring of the aforementioned compounds. The synthesis and S-adenosylhomocysteine hydrolase inhibitory and antiviral properties of these targets are described. Some, but not all, compounds in this series showed significant activity toward herpes, arena

  天然存在的基于腺嘌呤的碳环核苷阿里霉素和奈普罗星的3-deaza类似物具有尚未优化的生物学特性。在这个方向上，本文报道了上述化合物在3-deazaadenine环的C-2和C-3位置上的氟原子和C-3位置上的甲基的战略位置。描述了这些靶标的合成和S-腺苷同型半胱氨酸水解酶的抑制和抗病毒特性。该系列中的某些（但不是全部）化合物对疱疹，竞技场，布尼亚，黄病毒和正粘病毒显示出显着活性。
• Synthetic studies towards (�)-aristeromycin and its 5?-homo-analogue
  作者：H. Kapeller、H. Baumgartner、H. Griengl

  DOI：10.1007/bf00807308

  日期：1997.2

  A new synthetic pathway to the carbocyclic nucleoside analogues (+/-)-aristeromycin (15) and its 5'-home-derivative (17) has been developed starting form norborn-5-en-2-one using nucleophilic substitution of a sulfonate ester group by the aglycone.
• Enantiospecific Synthesis of Carbocyclic Aminoimidazole Carboxamide Ribonucleotide (C-AICAR), Succinoaminoimidazole Carboxamide Ribonucleotide (C-SAICAR), and a New Intermediate for SAICAR Analogs
  作者：Laurent Schmitt、Carol A. Caperelli

  DOI：10.1080/15257779508010715

  日期：1995.11

  The (-)-enantiomer of the carbocyclic analogs of aminoimidazole carboxamide ribonucleotide (C-AlCAR(1), 7), and succinoaminoimidazole carboxamide ribonucleotide (C-SAlCAR, 14) have been prepared. En route, a new intermediate (19) for the preparation of SAlCAR analogs was developed.
• 3-Bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin: Synthesis and antiviral activity
  作者：Chong Liu、Qi Chen、Stewart W. Schneller

  DOI：10.1016/j.bmcl.2012.06.075

  日期：2012.8

  As an outgrowth of our program to explore 3-deazaadenine carbocyclic nucleosides, 3-bromo-3-deazaneplanocin (5) and 3-bromo-3-deazaaristeromycin (6) have been synthesized from a readily available cyclopentenol and cyclopentanone and either 4-amino- or 4-chloro-1H-imidazo[4,5-c]pyridine (6-amino- or 6-chloro-3-deazaadenine) in 5 steps and 7 steps, respectively. Antiviral analysis found 5 to display significant activity towards a number of (-)-ssRNA and a few dsDNA viruses. Compound 6 was less active than 5 against selected examples of those viruses affected by 5. (c) 2012 Elsevier Ltd. All rights reserved.