Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-6-ethylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester | 263243-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-6-ethylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS: 263243-35-2
• 化学式: C₂₁H₂₉NO₉S₂
• 分子量: 503.595
• InChiKey: XFVZUQZOLWUQDQ-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  134.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-6-ethylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 在 4-二甲氨基吡啶 、 sodium methylate 、 对甲苯磺酸 、 巯基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.5h， 生成 ethyl 2-acetamido-6-S-(5-tert-butoxycarbonylamino-5-deoxy-β-D-arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-d-arabinopyranosyl)-2-deoxy-1,6-dithio-β-d-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide

  摘要：

  A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.

  DOI：

  10.1016/s0008-6215(99)00253-0
• 作为产物：
  描述：

  乙酸酐 、 对甲苯磺酰氯 、 乙基2-乙酰氨基-2-脱氧- 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 13.0h， 以65%的产率得到Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-6-ethylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-d-arabinopyranosyl)-2-deoxy-1,6-dithio-β-d-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide

  摘要：

  A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.

  DOI：

  10.1016/s0008-6215(99)00253-0