(2S,3R)-4-O-benzoyl-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol | 132235-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-4-O-benzoyl-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol
• 英文别名: (2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-3-(2-propenyl)-1,2,4-butanetriol；(2S,3R)-4-O-Benzoyl-1-O-p-bromobenzyl-3-C-(2'-propenyl)-1,2,4-butan-triol；[(2R)-2-[(1S)-2-[(4-bromophenyl)methoxy]-1-hydroxyethyl]pent-4-enyl] benzoate
• CAS: 132235-67-7
• 化学式: C₂₁H₂₃BrO₄
• 分子量: 419.315
• InChiKey: CWWAICVXERVJDM-UYAOXDASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-4-O-benzoyl-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol 在 盐酸 、 sodium periodate 、 四氧化锇 、 氨 、 sodium 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 1.17h， 生成 2',3'-二脱氧-3'-(羟甲基)胞苷
  参考文献：
  名称：

  Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV

  摘要：

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.

  DOI：

  10.1021/jo00009a012
• 作为产物：
  描述：

  (2S,3R)-4-(p-bromobenzyloxy)-2,3-epoxybutan-1-ol 在 吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3R)-4-O-benzoyl-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol
  参考文献：
  名称：

  Synthesis of 4-C-hydroxymethyl hexopyranosyl nucleosides as potential inhibitors of HIV

  摘要：

  The synthesis of 1-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)thymine (13), -uracil (15), -cytosine (16) and 9-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)adenine (18) are described. The nucleoside analogues were evaluated for their anti-HIV activity in vitro.

  DOI：

  10.1016/s0040-4020(01)96269-6

文献信息

• US5215970A
  申请人：——

  公开号：US5215970A

  公开（公告）日：1993-06-01
• US5409906A
  申请人：——

  公开号：US5409906A

  公开（公告）日：1995-04-25
• [EN] NUCLEOSIDE DERIVATIVES
  申请人：MEDIVIR AB

  公开号：WO1992006102A1

  公开（公告）日：1992-04-16

  (EN) Novel antiviral compounds of formulae (1A) and (1B), wherein X and R1-R4 are as stated in claim 1 in the form of an $g(a)- or $g(b)-anomer or a mixture thereof, and pharmaceutically acceptable salts thereof are disclosed, as well as a new method for preparation thereof. Said compounds can be used for treatment of infections caused by viruses requiring reverse transcriptase for replication, such as HIV and hepatitis B virus.(FR) Nouveaux composés antiviraux de la formule (I) dans laquelle X et R1-R4 représentent comme énoncé dans la revendication 1, un anomère alpha ou bêta ou un mélange desdits anomères, et des sels pharmaceutiquement acceptables de ces substances. On décrit aussi une nouvelle méthode pour préparer ces composés. Lesdits composés peuvent être utilisés pour le traitement d'infections causées par des virus requérant la transcriptase inverse pour la réplication, tels que le VIH et le virus de l'hépatite B.
• Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV
  作者：Lars Svansson、Ingemar Kvarnstroem、Bjoern Classon、Bertil Samuelsson

  DOI：10.1021/jo00009a012

  日期：1991.4

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.
• Synthesis of 4-C-hydroxymethyl hexopyranosyl nucleosides as potential inhibitors of HIV
  作者：Magnus Björsne、Björn Classon、ngemar Kvarnström、Bertil Samuelsson

  DOI：10.1016/s0040-4020(01)96269-6

  日期：1993.9

  The synthesis of 1-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)thymine (13), -uracil (15), -cytosine (16) and 9-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)adenine (18) are described. The nucleoside analogues were evaluated for their anti-HIV activity in vitro.