1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside | 1203584-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside
• 英文别名: tert-butyldiphenylsilyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose；tert-butyldiphenylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside；Whlhcdsluaaptj-acfiuoazsa-；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-amino-6-[tert-butyl(diphenyl)silyl]oxyoxan-2-yl]methyl acetate
• CAS: 1203584-54-6
• 化学式: C₂₈H₃₇NO₈Si
• 分子量: 543.689
• InChiKey: WHLHCDSLUAAPTJ-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 caesium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents

  摘要：

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.

  DOI：

  10.1080/07328300903105108
• 作为产物：
  描述：

  2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 吡啶 、 咪唑 、 溶剂黄146 、 苄胺 、 锌 作用下， 生成 1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside
  参考文献：
  名称：

  在水介质中的非对映和对映选择性直接羟醛反应：一种新型的高效脯氨酸-糖嵌合催化剂

  摘要：

  提出了一种新的合成催化剂，其能够在直接的醛醇缩合反应中像酶一样起作用。据报道，将环己酮催化添加到各种取代的苯甲醛中，在化学收率和非对映体/对映异构体比例方面均取得了优异的结果。

  DOI：

  10.1002/adsc.201100143

文献信息

• New phosphine-imine and phosphine-amine ligands derived from d -gluco-, d -galacto- and d -allosamine in Pd-catalysed asymmetric allylic alkylation
  作者：Izabela Szulc、Robert Kołodziuk、Anna Zawisza

  DOI：10.1016/j.tet.2018.02.009

  日期：2018.3

  New phosphine-imine and phosphine-amine chiral ligands which were easily prepared from d-gluco-, d-galacto- and d-allosamine furnished a high level of enantiomeric excess (up to 99%) in the Pd(0)-catalysed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with malonates.

  容易从d-葡萄糖-，d-半乳糖和d- allosamine制备的新的膦-亚胺和膦-胺手性配体在Pd（0）催化的不对称中提供了高水平的对映体过量（最高达99％）。外消旋的1，3-二苯基-2-丙烯基乙酸酯与丙二酸酯的烯丙基烷基化。
• d-Glucosamine in a chimeric prolinamide organocatalyst for direct asymmetric aldol addition
  作者：Mauro De Nisco、Silvana Pedatella、Semiha Bektaş、Ada Nucci、Romualdo Caputo

  DOI：10.1016/j.carres.2012.03.041

  日期：2012.7

  O-TBDPS D-glucosamine coupled with L-proline is reported to act as an efficient organocatalyst in the accomplishment of direct aldol reactions. Excellent results, in terms of chemical yields, as well as diastereomeric and enantiomeric ratios, are reported for the catalyzed additions of cyclohexanone and acetone to variously substituted benzaldehydes. (C) 2012 Elsevier Ltd. All rights reserved.

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