2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose | 120489-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose
• 英文别名: pivaloyl(-3)[pivaloyl(-4)][pivaloyl(-6)]GlcNAc(b)-O-pivaloyl；[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 120489-55-6
• 化学式: C₂₈H₄₇NO₁₀
• 分子量: 557.682
• InChiKey: QCZYOFNEBBICEQ-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  苯硫酚 、 2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose 在 indium(III) chloride 作用下， 以88 %的产率得到phenyl 2-N-acetamido-2-deoxy-3,4,6-tri-O-pivaloyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  d-氨基葡萄糖和d-半乳糖胺β-构型硫代糖苷的形成及受保护的母乳低聚糖的合成

  摘要：

  我们报道了使用催化和无溶剂方法从d - N-乙酰葡糖胺立体选择性多克规模制备 2-叠氮基-2-脱氧-β-d-葡萄糖-和吡喃半乳糖苷的环己基-和苯基硫代糖苷。两种制备的结构单元被用作合成受保护形式的人乳低聚糖 LNT 和 LNnT 的关键中间体。

  DOI：

  10.1021/acs.joc.3c01267
• 作为产物：
  描述：

  D-GlcNAc 生成 2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose
  参考文献：
  名称：

  LJEVAKOVIC, DURDICA;TOMIC, SRDANKA;TOMASIC, JELKA, CARBOHYDR. RES., 182,(1988) N 2, C. 197-205

  摘要：

  DOI：

文献信息

• Selective pivaloylation of 2-acetamido-2-deoxy sugars
  作者：Đurđica Ljevaković、Srdanka Tomić、Jelka Tomašić

  DOI：10.1016/0008-6215(88)84003-5

  日期：1988.11

  Selective pivaloylation of 2-acetamido-2-deoxy-D-glucose, its methyl alpha- and beta-glycosides, and the methyl alpha-glycoside of N-acetyl-D-muramic acid under various conditions has been studied. The structures of the products were established by 1H-n.m.r. spectroscopy and acetylation. The orders of acylation, HO-6 greater than HO-3 greater than HO-1 greater than HO-4 for 2-acetamido-2-deoxy-D-glucose

  已经研究了在各种条件下2-乙酰氨基-2-脱氧-D-葡萄糖，其甲基α-和β-糖苷以及N-乙酰基-D-山梨酸的甲基α-糖苷的选择性聚乙烯醇化。通过1H-nmr光谱和乙酰化确定产物的结构。酰化的顺序是：对于2-乙酰氨基-2-脱氧-D-葡萄糖，HO-6大于HO-3大于HO-1大于HO-1，对于HO2大于HO-4大于HO-3。建立了它的甲基糖苷。2-乙酰氨基-2-脱氧-3,6-二-O-新戊酰-吡喃葡萄糖苷和2-乙酰氨基-2-脱氧-1,3,4,6-四-O-新戊酰甲基-D-吡喃葡萄糖被兔血清酯酶水解。
• An efficient conversion of N-acetyl-d-glucosamine to N-acetyl-d-galactosamine and derivatives
  作者：Jianhao Feng、Chang-Chun Ling

  DOI：10.1016/j.carres.2010.09.008

  日期：2010.11

  2-Acetamido-2-deoxy-D-galactose (D-GalNAc) is an important monosaccharide widely distributed in nature. However, unlike its 4-epimer, the 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), D-GalNAc is very expensive to obtain from commercial sources. Herein we report an efficient transformation that allows for the conversion of D-GlcNAc to a D-GalNAc derivative 7 in three steps and in 58.4-75% overall yields. The process was carried out on a greater than 20-g scale without the need of chromatography. The versatility of compound 7 was demonstrated by the synthesis of several useful monosaccharides and thiodisaccharides containing a D-GalNAc residue. (C) 2010 Elsevier Ltd. All rights reserved.