N⁷-tert-butoxycarbonyl-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-8-oxoadenosine | 439097-92-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁷-tert-butoxycarbonyl-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-8-oxoadenosine
• 英文别名: tert-butyl 9-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-amino-8-oxopurine-7-carboxylate
• CAS: 439097-92-4
• 化学式: C₂₄H₃₉N₅O₇Si
• 分子量: 537.688
• InChiKey: UHYXXNOUYVRXBZ-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N⁷-tert-butoxycarbonyl-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-8-oxoadenosine 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 5'-O-tert-butyldimethylsilyl-6-N-[N-[3,6-dioxa-8-aminooctyl]carbamoyl]-2',3'-O-isopropylidene-7,8-dihydro-8-oxoadenosine
  参考文献：
  名称：

  Synthesis of a biotin-conjugate of phosmidosine O-ethyl ester as a G1 arrest antitumor drug

  摘要：

  This paper deals with the synthesis of a stable biotin-phosmidosine conjugate molecule 3 that is required for isolation of biomolecules that bind to phosmidosine (1). It was found that introduction of a biotin residue into the 6-N position of phosmidosine could be carried out by reaction of an N-7-Boc-7,8-dihydro-8-oxoadenosine derivative 13 with phenyl chloroformate followed by displacement with a diamine derivative 6 along with the simultaneous removal of the Boc group and one of the two phenoxycarbonyl groups and the successive condensation with an N-tritylated biotin derivative 5. The condensation of an N-prolylphosphorodiamidite derivative 4 with an appropriately protected 7,8-dihydro-8-oxoadenosine derivative 17 having the biotin residue gave the coupling product 18, which was deprotected to give the biotin-phosmidosine (O-ethyl ester) conjugate 3. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.037
• 作为产物：
  描述：

  8-氧腺苷 在 吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 生成 N⁷-tert-butoxycarbonyl-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-8-oxoadenosine
  参考文献：
  名称：

  膦酰胺及其相关化合物的首次合成及其抗癌活性。

  摘要：

  本文描述了膦酰胺和膦嘧啶B的首次合成，即由8-氧代腺苷和L-脯氨酸组成的核苷酸抗生素，它们通过独特的N-酰基氨基磷酸酯键连接。膦酰胺在N-酰基氨基磷酸酯键的磷原子上具有尚未确定的手性中心。磷肌苷B是一种脱磷的磷肌苷衍生物，在磷上没有手性。在5-（3,5-二硝基苯基）-1H-四唑存在下，N-乙酰基-8-氧代腺苷5'-O-亚磷酰胺衍生物与N-保护的脯氨酰胺反应成功地合成了肌苷B。通过使用叔丁氧羰基（Boc）基团可以成功合成膦嘧啶 发现它被选择性地引入到8-氧代腺苷的7-NH官能团中，并由于其空间效应而以未保护的6-氨基未被磷酸化的方式用作假保护基团。8-氧代腺苷5'-亚磷酰胺衍生物与N-三苯甲基脯氨酰胺的最终偶联反应，然后完全脱保护，得到膦酰胺及其非对映异构体的混合物。非对映异构体的（13）C NMR光谱表明，缓慢洗脱的非对映异构体1b是天然存在的膦酰胺。通过MTT分析评价了膦肌苷1b，其非对

  DOI：

  10.1021/jo016176g

文献信息

• First Synthesis and Anticancer Activity of Phosmidosine and Its Related Compounds
  作者：Tomohisa Moriguchi、Norio Asai、Kazuhisa Okada、Kohji Seio、Takuma Sasaki、Mitsuo Sekine

  DOI：10.1021/jo016176g

  日期：2002.5.1

  the presence of 5-(3,5-dinitrophenyl)-1H-tetrazole. The successful synthesis of phosmidosine was achieved by use of a tert-butoxycarbonyl (Boc) group, which was found to be selectively introduced into the 7-NH function of 8-oxoadenosine and to serve as a pseudo-protecting group due to its steric effect in such manner that the unmasked 6-amino group was not phosphitylated. Final coupling reaction of the

  本文描述了膦酰胺和膦嘧啶B的首次合成，即由8-氧代腺苷和L-脯氨酸组成的核苷酸抗生素，它们通过独特的N-酰基氨基磷酸酯键连接。膦酰胺在N-酰基氨基磷酸酯键的磷原子上具有尚未确定的手性中心。磷肌苷B是一种脱磷的磷肌苷衍生物，在磷上没有手性。在5-（3,5-二硝基苯基）-1H-四唑存在下，N-乙酰基-8-氧代腺苷5'-O-亚磷酰胺衍生物与N-保护的脯氨酰胺反应成功地合成了肌苷B。通过使用叔丁氧羰基（Boc）基团可以成功合成膦嘧啶 发现它被选择性地引入到8-氧代腺苷的7-NH官能团中，并由于其空间效应而以未保护的6-氨基未被磷酸化的方式用作假保护基团。8-氧代腺苷5'-亚磷酰胺衍生物与N-三苯甲基脯氨酰胺的最终偶联反应，然后完全脱保护，得到膦酰胺及其非对映异构体的混合物。非对映异构体的（13）C NMR光谱表明，缓慢洗脱的非对映异构体1b是天然存在的膦酰胺。通过MTT分析评价了膦肌苷1b，其非对
• Synthesis of a biotin-conjugate of phosmidosine O-ethyl ester as a G1 arrest antitumor drug
  作者：Mitsuo Sekine、Kazuhisa Okada、Kohji Seio、Tohru Obata、Takuma Sasaki、Hideaki Kakeya、Hiroyuki Osada

  DOI：10.1016/j.bmc.2004.09.037

  日期：2004.12

  This paper deals with the synthesis of a stable biotin-phosmidosine conjugate molecule 3 that is required for isolation of biomolecules that bind to phosmidosine (1). It was found that introduction of a biotin residue into the 6-N position of phosmidosine could be carried out by reaction of an N-7-Boc-7,8-dihydro-8-oxoadenosine derivative 13 with phenyl chloroformate followed by displacement with a diamine derivative 6 along with the simultaneous removal of the Boc group and one of the two phenoxycarbonyl groups and the successive condensation with an N-tritylated biotin derivative 5. The condensation of an N-prolylphosphorodiamidite derivative 4 with an appropriately protected 7,8-dihydro-8-oxoadenosine derivative 17 having the biotin residue gave the coupling product 18, which was deprotected to give the biotin-phosmidosine (O-ethyl ester) conjugate 3. (C) 2004 Elsevier Ltd. All rights reserved.