O-tert-butyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 13035-50-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-tert-butyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: tert-butyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；tert-butyl-(tetra-O-acetyl-α-D-glucopyranoside)；tert-Butyl-(tetra-O-acetyl-α-D-glucopyranosid)；2,3,4,6-Tetra-O-acetyl-tert.-butyl-α-D-glucopyranosid；tert.-Butyl-2.3.4.6-tetra-O-acetyl-α-D-glucopyranosid；tert.-Butyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose；1-O-(tert-Butyl)-2,3,4,6-tetra-O-acetyl-alpha-d-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2-methylpropan-2-yl)oxy]oxan-2-yl]methyl acetate
• CAS: 13035-50-2
• 化学式: C₁₈H₂₈O₁₀
• 分子量: 404.414
• InChiKey: XAQFMMJQMZESRB-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  tert-butyl-(tetra-O-acetyl-β-D-glucopyranoside) 在 硫酸 、 乙酸酐 、 溶剂黄146 作用下， 生成 O-tert-butyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Lindberg, Acta Chemica Scandinavica (1947), 1949, vol. 3, p. 1153,1168

  摘要：

  DOI：

文献信息

• The tertiary-butyl group: Selective protection of the anomeric centre and evaluation of its orthogonal cleavage
  作者：Afraz Subratti、Nigel Kevin Jalsa

  DOI：10.1016/j.tetlet.2018.04.048

  日期：2018.5

  The tertiary-butyl group has not been examined extensively as a protecting group. In this work, we describe the synthesis of tert-butyl glycosides via the Fischer glycosylation protocol. Furthermore, its utility as a temporary anomeric protecting group was evaluated. A range of differentially protected monosaccharides was used to investigate the stability of the tert-butyl group upon the introduction

  在第三丁基组尚未被广泛讨论的一个保护基。在这项工作中，我们描述了通过Fischer糖基化方案合成叔丁基糖苷。此外，评估了其作为临时端基保护基的用途。一系列差异保护的单糖用于研究引入其他保护基团后叔丁基的稳定性。在后者存在下其裂解的相容性。
• Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger
  作者：Xiangying Gu、Lin Chen、Xin Wang、Xiao Liu、Qidong You、Wenwei Xi、Li Gao、Guohua Chen、Yue-Lei Chen、Bing Xiong、Jingkang Shen

  DOI：10.1021/jo402551x

  日期：2014.2.7

  A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
• NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: a tunable access to either 2-deoxy sugars or 1,5-anhydro-itols
  作者：Isabelle Bruyère、Zoltan Tóth、Hamida Benyahia、Jia Lu Xue、Jean-Pierre Praly

  DOI：10.1016/j.tet.2013.09.032

  日期：2013.11

  UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-D-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranose were achieved upon heating to 80 degrees C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (D-galacto), but some (D-manno, 5-thio-D-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light. (c) 2013 Elsevier Ltd. All rights reserved.
• Lindberg, Acta Chemica Scandinavica (1947), 1948, vol. 2, p. 534,535
  作者：Lindberg

  DOI：——

  日期：——
• LACOMBE, JEAN-MICHEL;RAKOTOMANOMANA, NJARA;PAVIA, ANDRE, J. CARBOHYDR. CHEM., 9,(1990) N, C. 85-92
  作者：LACOMBE, JEAN-MICHEL、RAKOTOMANOMANA, NJARA、PAVIA, ANDRE

  DOI：——

  日期：——