(4aR,6R,7R,8R,8aR)-2,2-ditert-butyl-6-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasiline-7,8-diol | 198958-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6R,7R,8R,8aR)-2,2-ditert-butyl-6-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasiline-7,8-diol
• CAS: 198958-39-3
• 化学式: C₁₅H₃₀O₆Si
• 分子量: 334.485
• InChiKey: JUEZEBXLPLYZIB-NJMOYASZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  22
• 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：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7R,8R,8aR)-2,2-ditert-butyl-6-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasiline-7,8-diol 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 2,3-di-O-benzyl-β-D-galactopyranoside
  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 、 甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 1-羟基苯并三唑 作用下， 以87%的产率得到(4aR,6R,7R,8R,8aR)-2,2-ditert-butyl-6-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasiline-7,8-diol
  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

• General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2-<i>trans</i>-Diols to 1,2-<i>cis</i>-Diols
  作者：Xiaolei Li、Jicheng Wu、Weiping Tang

  DOI：10.1021/jacs.1c13399

  日期：2022.3.2

  Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters

  人聚糖主要由九种常见的糖组成部分组成。另一方面，已经在细菌中发现了数百种单糖，其中大多数不易获得。获得这些稀有糖和相应的糖缀合物的能力可以促进对细菌中各种重要的生物学过程的研究，包括微生物群与人类宿主之间的相互作用。许多稀有糖也存在于各种具有显着生物活性的天然产物和药物试剂中。尽管已经开发了几种用于合成稀有单糖的方法，但其中大多数都涉及冗长的步骤。在此处，反式二醇到 1,2-顺式二醇。硼酸酯的形成将平衡推向 1,2-顺式二醇产物，该产物可立即用于进一步的选择性功能化和糖基化。通过在天然产物或生物活性化合物中有效构建糖苷骨架，证明了该策略的实用性。
• 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.