2-azido-2-deoxy-β-D-galactopyranosyl fluoride | 335105-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-2-deoxy-β-D-galactopyranosyl fluoride
• 英文别名: 2-Azido-2-deoxy-I(2)-D-galactopyranosyl fluoride；(2R,3R,4R,5R,6S)-5-azido-6-fluoro-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 335105-68-5
• 化学式: C₆H₁₀FN₃O₄
• 分子量: 207.162
• InChiKey: QITBSTANSWXBAR-VFUOTHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azido-2-deoxy-β-D-galactopyranosyl fluoride 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 二氯二茂锆 、 三氟甲磺酸三甲基硅酯 、 氢气 、 silver perchlorate 、 1-羟基苯并三唑 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 26.83h， 生成 T表位,丝氨酰
  参考文献：
  名称：

  Cyclic di-t-butylsilylenediyl ether group as a convenient protective group for the glycoconjugate synthesis

  摘要：

  Treatment of methyl B-D-glucopyranoside, methyl alpha -D-glucopyranoside, 2-azido-2-deoxy-beta -D-galactopyranosyl fluoride, and 1,6-anhydro-beta -lactose with di-t-butyldichlorosilane gave the corresponding 4.6-cyclic di-t-butylsilylenediyl ether (4,6-CDBS) derivatives in high yields. It was suggested that the 4,6-CDBS group is quite stable under general conditions for further chemical manipulations such as the acetylation, benzylation and glycosylation reactions employed widely in the carbohydrate chemistry. This protective group was readily removed by treatment with tetrabutylammonium fluoride or triethylamine-3HF complex under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00044-2
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate 在 sodium methylate 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 22.0h， 生成 2-azido-2-deoxy-β-D-galactopyranosyl fluoride
  参考文献：
  名称：

  Efficient and versatile synthesis of mucin-like glycoprotein mimics

  摘要：

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01359-5

文献信息

• Efficient and versatile synthesis of mucin-like glycoprotein mimics
  作者：Yuki Tachibana、Naoki Matsubara、Fumio Nakajima、Tetsuro Tsuda、Sakae Tsuda、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1016/s0040-4020(02)01359-5

  日期：2002.12

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Cyclic di-t-butylsilylenediyl ether group as a convenient protective group for the glycoconjugate synthesis
  作者：Daijyu Kumagai、Masaki Miyazaki、Shin-Ichiro Nishimura

  DOI：10.1016/s0040-4039(01)00044-2

  日期：2001.3

  Treatment of methyl B-D-glucopyranoside, methyl alpha -D-glucopyranoside, 2-azido-2-deoxy-beta -D-galactopyranosyl fluoride, and 1,6-anhydro-beta -lactose with di-t-butyldichlorosilane gave the corresponding 4.6-cyclic di-t-butylsilylenediyl ether (4,6-CDBS) derivatives in high yields. It was suggested that the 4,6-CDBS group is quite stable under general conditions for further chemical manipulations such as the acetylation, benzylation and glycosylation reactions employed widely in the carbohydrate chemistry. This protective group was readily removed by treatment with tetrabutylammonium fluoride or triethylamine-3HF complex under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.