5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol | 182550-30-7

• 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: 5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol
• 英文别名: (2R,3R,4R)-5-azido-2,3,4-tris(phenylmethoxy)pentan-1-ol
• CAS: 182550-30-7
• 化学式: C₂₆H₂₉N₃O₄
• 分子量: 447.534
• InChiKey: LCMHAZJZPARXMX-TWJOJJKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol 在 lithium aluminium tetrahydride 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 cyclohexyl 2,3,4-tri-O-benzyl-5-tert-butylmethyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside
  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：

  1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose 在 sodium tetrahydroborate 、 sodium azide 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.33h， 生成 5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol
  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

文献信息

• Two efficient routes for construction of amidine-linked pseudo-disaccharide
  作者：Katsuhiko Suzuki、Takashi Fujii、Ken-ichi Sato、Hironobu Hashimoto

  DOI：10.1016/0040-4039(96)01277-4

  日期：1996.8

  Two routes for the synthesis of the amidine-linked pseudo-disaccharide were developed. The amidine linkage was constructed by the intermolecular or intramolecular coupling between thioamide and amine in the presence of mercury (II) chloride. The former construction from d-arabinono-1,5-thiolactam and 6-amino-6-deoxy-d-glucoside gave the corresponding pseudo-disaccharide. The latter construction of

  开发了两种方法合成the连接的假二糖。通过在氯化汞（II）存在下硫酰胺和胺之间的分子间或分子内偶联来构建am键。d-阿拉伯糖基-1,5-硫代内酰胺和6-氨基-6-脱氧-d-葡萄糖苷的前一种结构给出了相应的假二糖。在4-（5-氨基-5-脱氧-d-硫代阿拉伯氨酰基）氨基-4-脱氧-d-葡糖苷的情况下证明了linkage键的后一种结构。
• 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
  作者：Katsuhiko Suzuki、Hironobu Hashimoto

  DOI：10.1016/s0008-6215(99)00253-0

  日期：1999.1

  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.