1,2,3-tri-O-acetyl-5-O-methylsulfonyl-D-arabinofuranose | 263243-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-tri-O-acetyl-5-O-methylsulfonyl-D-arabinofuranose
• 英文别名: 1,2,3-tri-O-acetyl-5-O-mesyl-D-arabinofuranose
• CAS: 263243-20-5
• 化学式: C₁₂H₁₈O₁₀S
• 分子量: 354.335
• InChiKey: NYTDHQYAUPGMMY-YIBTVLSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.89
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-5-O-methylsulfonyl-D-arabinofuranose 在 sodium tetrahydroborate 、 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 29.5h， 生成 5-azido-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
• 作为产物：
  描述：

  甲基磺酰氯 、 1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose 以 吡啶 为溶剂， 反应 0.33h， 以79%的产率得到1,2,3-tri-O-acetyl-5-O-methylsulfonyl-D-arabinofuranose
  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

• A Simple Synthesis of C-8 Modified 2-Keto-3-deoxy-d-manno-octulosonic Acid (KDO) Derivatives
  作者：Milton Kiefel、Renee Winzar、Jessica Philips

  DOI：10.1055/s-0029-1219356

  日期：2010.3

  This paper describes a simple and efficient method with which to prepare C-8 modified 2-keto-3-deoxy-d-manno-octulosonic acid (KDO) derivatives from C-5 modified arabinose derivatives.

  本文描述了一种简单高效的方法，可以从C-5修饰的阿拉伯糖衍生物制备C-8修饰的2-酮-3-脱氧-d-甘露-壬酸（KDO）衍生物。