4,6-di-O-acetyl-1-O-benzyl-2-deoxy-2-N-acetyl-β-D-glucopyranosid[2,3-d]-1,3-oxazolidin-2-one | 853059-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-di-O-acetyl-1-O-benzyl-2-deoxy-2-N-acetyl-β-D-glucopyranosid[2,3-d]-1,3-oxazolidin-2-one
• 英文别名: benzyl 2-N-acetyl-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-β-D-glucopyranoside；[(3aR,4R,6R,7S,7aR)-3-acetyl-7-acetyloxy-2-oxo-4-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-6-yl]methyl acetate
• CAS: 853059-02-6
• 化学式: C₂₀H₂₃NO₉
• 分子量: 421.404
• InChiKey: QCOAGKOAKQBYJE-FVVUREQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,6-di-O-acetyl-1-O-benzyl-2-deoxy-2-N-acetyl-β-D-glucopyranosid[2,3-d]-1,3-oxazolidin-2-one 在 碳酸氢铵 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以82%的产率得到Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-6-benzyloxy-4-hydroxy-5-ureido-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Chemoselective deprotection and functional group interconversion of ring-fused 2N,3O-oxazolidinones of N-acetyl-d-glucosamine

  摘要：

  These studies describe the chemoselective deprotection of trans-fused 2N,3O-oxazolidinone derivatives of N-acetyl-beta-D-glucosamine. Selective opening of the oxazolidinone ring or N-deacetylation without ring opening is demonstrated. Certain amines are shown to efficiently afford C-2 ureido sugars under mild conditions. This work demonstrates the high degree of chemoselective manipulation possible with ring-fused 2N,3O-oxazolidinone derivatives of N-acetyl-D-glucosamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.013
• 作为产物：
  描述：

  p-tolyl 4,6-di-O-acetyl-2-deoxy-1-thio-β-D-glucopyranosid[2,3-d]-1,3-oxazolidin-2-one 在 3 A molecular sieve 吡啶 、 4-二甲氨基吡啶 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 4,6-di-O-acetyl-1-O-benzyl-2-deoxy-2-N-acetyl-β-D-glucopyranosid[2,3-d]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Factors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-d-glucosamine

  摘要：

  It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acetyl-D-glucosamine undergoes high-yield glycosidation under mild donor activation conditions. Stereoselective formation of alpha-linked or beta-linked glycosides is dependent on reactivity of acceptor alcohols, where rate of glycosidation correlates to stereochemical outcome. Evidence for the role of glycosyl triflate intermediates and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochemical control is presented.

  DOI：

  10.1021/jo047812o

文献信息

• Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
  作者：Toshiki Nokami、Akito Shibuya、Yoshihiro Saigusa、Shino Manabe、Yukishige Ito、Jun-ichi Yoshida

  DOI：10.3762/bjoc.8.52

  日期：——

  Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products.

  用低温电化学氧化从硫代糖苷生成带有2,3-噁唑啉醇保护基的糖基三氟甲磺酸酯。糖基三氟甲磺酸酯与醇在低温下反应，选择性地形成相应的糖苷β-选择性产物。然而，在高温反应条件下，在无碱存在的情况下观察到α-选择性。原位生成的三氟甲磺酸促进β-产物向α-产物的异构化。