Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-(2-acetoxymethoxy-ethoxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-4-yl ester | 190779-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-(2-acetoxymethoxy-ethoxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-4-yl ester
• CAS: 190779-59-0
• 化学式: C₂₄H₃₂O₁₂
• 分子量: 512.511
• InChiKey: SOWLDYBCPCIUKA-SJSRKZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-(2-acetoxymethoxy-ethoxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-4-yl ester 在 钯 吡啶 、 四氮唑 、 叔丁基过氧化氢 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 36.35h， 生成 Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-hydroxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester
  参考文献：
  名称：

  Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

  摘要：

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00309-8
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-pyran-4-yl ester 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 吡啶盐酸盐 、 乙酸酐 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 17.08h， 生成 Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-(2-acetoxymethoxy-ethoxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

  摘要：

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00309-8