2(S)-[N-(thymin-1-ylacetyl)amino]-1(S)-phenyl-1,3-propanediol | 202129-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2(S)-[N-(thymin-1-ylacetyl)amino]-1(S)-phenyl-1,3-propanediol
• 英文别名: N-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide
• CAS: 202129-68-8
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: ACVQWLIZHBYJGU-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(S)-[N-(thymin-1-ylacetyl)amino]-1(S)-phenyl-1,3-propanediol 在 吡啶 、 四氮唑 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 N-[(1R,2S)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-1-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-1-phenylpropan-2-yl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide
  参考文献：
  名称：

  Oligonucleotides with ( N -thymin-1-ylacetyl)-1-arylserinol backbone: chiral acyclic analogs with restricted conformational flexibility

  摘要：

  All four threo/erythro stereoisomers of 2(R/S)-(N-thymin-1-ylacetyl)-amino-1(R/S)-aryl-1,3-propanediol were synthesized from 2(R/S)-amino-1(R/S)-aryl-1,3-propanediol in 45-50% overall yield. The inversion of the C1 hydroxyl group in (1S, 2S), 4a, and (1R, 2R), 4d, was accomplished under Mitsunobu conditions to get (IR, 2S), 4c, and (1S, 2R), 4e isomers, respectively Compounds 4a-f were individually converted into their respective amidite synthons 5a-f. All these stereoisomers were individually incorporated into oligonucleotides (ODNs) at pre-determined positions and various biophysical studies of their hybrids with complementary DNA were carried out. All the four stereoisomers when present at 3'/5' terminal positions in the ODNs were almost equally efficient in their binding capacity as the natural oligomers, with (1S, 2S) being marginally favored over other stereoisomers. The incorporation of these chiral acyclic nucleosides also protected the ODN against enzymatic degradation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01099-1
• 作为产物：
  描述：

  (1S,2S)-(+)-2-氨基-1-苯基-1,3-丙二醇 在 sodium carbonate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 2(S)-[N-(thymin-1-ylacetyl)amino]-1(S)-phenyl-1,3-propanediol
  参考文献：
  名称：

  Oligonucleotides with ( N -thymin-1-ylacetyl)-1-arylserinol backbone: chiral acyclic analogs with restricted conformational flexibility

  摘要：

  All four threo/erythro stereoisomers of 2(R/S)-(N-thymin-1-ylacetyl)-amino-1(R/S)-aryl-1,3-propanediol were synthesized from 2(R/S)-amino-1(R/S)-aryl-1,3-propanediol in 45-50% overall yield. The inversion of the C1 hydroxyl group in (1S, 2S), 4a, and (1R, 2R), 4d, was accomplished under Mitsunobu conditions to get (IR, 2S), 4c, and (1S, 2R), 4e isomers, respectively Compounds 4a-f were individually converted into their respective amidite synthons 5a-f. All these stereoisomers were individually incorporated into oligonucleotides (ODNs) at pre-determined positions and various biophysical studies of their hybrids with complementary DNA were carried out. All the four stereoisomers when present at 3'/5' terminal positions in the ODNs were almost equally efficient in their binding capacity as the natural oligomers, with (1S, 2S) being marginally favored over other stereoisomers. The incorporation of these chiral acyclic nucleosides also protected the ODN against enzymatic degradation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01099-1

文献信息

• Oligonucleotides with (N-thymin-1-ylacetyl) 1-phenylserinol in backbone: Chiral acyclic analogues that form dna triplexes
  作者：Vipul S. Rana、Vaijayanti A. Kumar、Krishma N. Ganesh

  DOI：10.1016/s0960-894x(97)10105-6

  日期：1997.11

  The synthesis of oligonucleotides containing chiral acyclic 2(R/S)-(N-thymin-1-ylacetyl)-amino-1(R/S)-phenyl-1,3-propanediol unit in the backbone (I, R=Ar) is described. When used as third strand of a triplex with complementary natural duplex, the modified oligonucleotides form stable triplexes with triplex double left right arrow duplex transition Tm dependent on the number, position and stereochemistry of modification. (C) 1997 Elsevier Science Ltd.
• Oligonucleotides with ( N -thymin-1-ylacetyl)-1-arylserinol backbone: chiral acyclic analogs with restricted conformational flexibility
  作者：Vipul S Rana、Vaijayanti A Kumar、Krishna N Ganesh

  DOI：10.1016/s0040-4020(00)01099-1

  日期：2001.2

  All four threo/erythro stereoisomers of 2(R/S)-(N-thymin-1-ylacetyl)-amino-1(R/S)-aryl-1,3-propanediol were synthesized from 2(R/S)-amino-1(R/S)-aryl-1,3-propanediol in 45-50% overall yield. The inversion of the C1 hydroxyl group in (1S, 2S), 4a, and (1R, 2R), 4d, was accomplished under Mitsunobu conditions to get (IR, 2S), 4c, and (1S, 2R), 4e isomers, respectively Compounds 4a-f were individually converted into their respective amidite synthons 5a-f. All these stereoisomers were individually incorporated into oligonucleotides (ODNs) at pre-determined positions and various biophysical studies of their hybrids with complementary DNA were carried out. All the four stereoisomers when present at 3'/5' terminal positions in the ODNs were almost equally efficient in their binding capacity as the natural oligomers, with (1S, 2S) being marginally favored over other stereoisomers. The incorporation of these chiral acyclic nucleosides also protected the ODN against enzymatic degradation. (C) 2001 Elsevier Science Ltd. All rights reserved.