(S)-2-(Toluene-4-sulfonylamino)-6-((2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-hexanoic acid benzyl ester | 1059579-93-9

• 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: (S)-2-(Toluene-4-sulfonylamino)-6-((2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-hexanoic acid benzyl ester
• 英文别名: benzyl (2S)-2-[(4-methylphenyl)sulfonylamino]-6-[(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]hexanoate
• CAS: 1059579-93-9
• 化学式: C₂₄H₃₁NO₈S
• 分子量: 493.578
• InChiKey: HXEVEQOCOBDYJS-QPDLBLOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-2-(Toluene-4-sulfonylamino)-6-((2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-hexanoic acid benzyl ester 在 sodium acetate 作用下， 反应 5.0h， 生成 Benzyl <5,6,7,8,9-pentadeoxy-9(S)-<(p-toluenesulfonyl)amino>-1,2,3-tri-O-acetyl>-α-D-ribo-decofuranuronate 、 Benzyl <5,6,7,8,9-pentadeoxy-9(S)-<(p-toluenesulfonyl)amino>-1,2,3-tri-O-acetyl>-β-D-ribo-decofuranuronate
  参考文献：
  名称：

  Syntheses of 6-Deaminosinefungin and (S)-6-Methyl-6-deaminosinefungin

  摘要：

  The nucleosides S-adenosylmethonine (SAM, AdoMet) and S-adenosylhomocysteine (SAH, AdoHcy) are involved in a number of important enzyme systems. The direct or indirect inhibition of these enzymes is currently of high interest, particularly in the areas of antiviral and cell proliferation research. We report here the first chirospecific syntheses of G(S)-methyl-6-deaminosinefungin (4) and 6-deaminosinefungin (5) which are analogues of SAM (1), SAH (2), and sinefungin (3). From ketone 6 (tert-butyl [methyl 2,3-O-isopropylidene-5,7,8,9-tetradeoxy-9(S)-[(p-toluenesulfonyl)amino]-beta-D-ribo-deculofuranosid]uronate), an intermediate in the sinefungin synthesis, the methylene derivative was prepared by using the tosylhydrazone-hydroboration method. Nucleoside formation with adenine and deprotection then led to 6-deaminosinefungin. For the synthesis of (S)-6-methyl-6-deaminosinefungin (4), ketone 6 was converted in four steps into the 6(S)-methyl derivative using a cuprate reagent. After the adenine was attached, an appropriate deprotection sequence yielded 4. Thus, 4 was synthesized in 11 steps from ketone 6 in an overall yield of 13%.

  DOI：

  10.1021/jo00094a033
• 作为产物：
  描述：

  (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 在 氢氟酸 盐酸 、 ammonium cerium(IV) nitrate 、 草酸 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 氯仿 为溶剂， 反应 92.0h， 生成 (S)-2-(Toluene-4-sulfonylamino)-6-((2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-hexanoic acid benzyl ester
  参考文献：
  名称：

  Syntheses of 6-Deaminosinefungin and (S)-6-Methyl-6-deaminosinefungin

  摘要：

  The nucleosides S-adenosylmethonine (SAM, AdoMet) and S-adenosylhomocysteine (SAH, AdoHcy) are involved in a number of important enzyme systems. The direct or indirect inhibition of these enzymes is currently of high interest, particularly in the areas of antiviral and cell proliferation research. We report here the first chirospecific syntheses of G(S)-methyl-6-deaminosinefungin (4) and 6-deaminosinefungin (5) which are analogues of SAM (1), SAH (2), and sinefungin (3). From ketone 6 (tert-butyl [methyl 2,3-O-isopropylidene-5,7,8,9-tetradeoxy-9(S)-[(p-toluenesulfonyl)amino]-beta-D-ribo-deculofuranosid]uronate), an intermediate in the sinefungin synthesis, the methylene derivative was prepared by using the tosylhydrazone-hydroboration method. Nucleoside formation with adenine and deprotection then led to 6-deaminosinefungin. For the synthesis of (S)-6-methyl-6-deaminosinefungin (4), ketone 6 was converted in four steps into the 6(S)-methyl derivative using a cuprate reagent. After the adenine was attached, an appropriate deprotection sequence yielded 4. Thus, 4 was synthesized in 11 steps from ketone 6 in an overall yield of 13%.

  DOI：

  10.1021/jo00094a033

文献信息

• Syntheses of 6-Deaminosinefungin and (S)-6-Methyl-6-deaminosinefungin
  作者：Patricia Peterli-Roth、Martin P. Maguire、Elisa Leon、Henry Rapoport

  DOI：10.1021/jo00094a033

  日期：1994.7

  The nucleosides S-adenosylmethonine (SAM, AdoMet) and S-adenosylhomocysteine (SAH, AdoHcy) are involved in a number of important enzyme systems. The direct or indirect inhibition of these enzymes is currently of high interest, particularly in the areas of antiviral and cell proliferation research. We report here the first chirospecific syntheses of G(S)-methyl-6-deaminosinefungin (4) and 6-deaminosinefungin (5) which are analogues of SAM (1), SAH (2), and sinefungin (3). From ketone 6 (tert-butyl [methyl 2,3-O-isopropylidene-5,7,8,9-tetradeoxy-9(S)-[(p-toluenesulfonyl)amino]-beta-D-ribo-deculofuranosid]uronate), an intermediate in the sinefungin synthesis, the methylene derivative was prepared by using the tosylhydrazone-hydroboration method. Nucleoside formation with adenine and deprotection then led to 6-deaminosinefungin. For the synthesis of (S)-6-methyl-6-deaminosinefungin (4), ketone 6 was converted in four steps into the 6(S)-methyl derivative using a cuprate reagent. After the adenine was attached, an appropriate deprotection sequence yielded 4. Thus, 4 was synthesized in 11 steps from ketone 6 in an overall yield of 13%.