(4aR,6S,7R,8R,8aR)-7-azido-2,2-ditert-butyl-6-fluoro-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-ol | 259236-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6S,7R,8R,8aR)-7-azido-2,2-ditert-butyl-6-fluoro-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-ol
• CAS: 259236-39-0
• 化学式: C₁₄H₂₆FN₃O₄Si
• 分子量: 347.462
• InChiKey: SQISDDIHPGAQFQ-PZWNZHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4aR,6S,7R,8R,8aR)-7-azido-2,2-ditert-butyl-6-fluoro-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-ol 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 、 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：

  二叔丁基氯硅烷 、 2-azido-2-deoxy-β-D-galactopyranosyl fluoride 在 吡啶 、 1-羟基苯并三唑 作用下， 以76%的产率得到(4aR,6S,7R,8R,8aR)-7-azido-2,2-ditert-butyl-6-fluoro-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-ol
  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

文献信息

• 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.