methyl-2-acetamido-3,4,6-tri-O-benzyl-2-desoxy-α-D-mannopyranoside | 117153-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-2-acetamido-3,4,6-tri-O-benzyl-2-desoxy-α-D-mannopyranoside
• 英文别名: methyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-mannopyranoside；N-[(2S,3S,4R,5S,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 117153-62-5
• 化学式: C₃₀H₃₅NO₆
• 分子量: 505.611
• InChiKey: UMJZGAQNQUVXLB-JPGUHONBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl-2-acetamido-3,4,6-tri-O-benzyl-2-desoxy-α-D-mannopyranoside 生成 methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-talo-pyranoside
  参考文献：
  名称：

  LAFONT, DOMINIQUE;DESCOTES, GRARD, CARBOHYDR. RES., 175,(1988) N 1, 35-48

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-3,4,6-tri-O-benzyl-2-desoxy-2-dimethylphosphoramido-α-D-mannopyranoside 生成 methyl-2-acetamido-3,4,6-tri-O-benzyl-2-desoxy-α-D-mannopyranoside
  参考文献：
  名称：

  LAFONT, DOMINIQUE;DESCOTES, GRARD, CARBOHYDR. RES., 175,(1988) N 1, 35-48

  摘要：

  DOI：

文献信息

• Nouvelle voie d'accès aux 1,2-trans-2-amino-2-désoxyglycopyranosides par l'intermédiaire des phosphoramidates de 1,2-trans-2-désoxy-2-iodoglycopyranosyles
  作者：Dominique Lafont、Gérard Descotes

  DOI：10.1016/0008-6215(88)80154-x

  日期：1988.4

  present in the medium. Use of simple alcohols yielded alkyl glycosides having β- d - gluco , β- d - xylo , α- d - manno , and α- d - lyxo configurations, respectively, starting from α- d - manno , α- d - lyxo , β- d - gluco , and β- d - xylo phosphoramidates, with excellent yields. The same reaction with an alcohol derived from galactopyranose led to the expected disaccharide with a low yield.

  摘要1,2-反式-2-脱氧-2-脱氧-2-碘基吡喃糖基氨基磷酸酯（由相应的糖类通过加入碘叠氮化物，然后与亚磷酸酯进行斯托丁格反应制得），通过在碱存在下用醇处理至相应的1在C-1和C-2处的构型反转后，， 2-反式-2-脱氧-2-磷酰胺基多聚核糖苷。反应通过氮丙啶中间体进行，该中间体被存在于介质中的醇打开。使用简单的醇可分别从α-d-甘露聚糖，α-d-lyxo，β-d-葡萄糖，β-d-木糖醇，α-d-甘露糖和α-d-lyxo构成烷基糖苷。 β-d-葡萄糖和β-d-木糖基氨基甲酸酯，具有优异的收率。与衍生自吡喃半乳糖的醇的相同反应导致低产率的预期二糖。
• Epoxidation of glycals with oxone–acetone–tetrabutylammonium hydrogen sulfate: a convenient access to simple β-d-glycosides and to α-d-mannosamine and d-talosamine donors
  作者：Dominique Lafont、Joseph D’Attoma、Rejane Gomez、Peter G. Goekjian

  DOI：10.1016/j.tetasy.2011.06.027

  日期：2011.6

  The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone-acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-beta-D-glycosides or 1,2-trans-beta-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido-2-deoxy-alpha-D-pyranosides or alkyl 2-allyloxycarbonylamino-2deoxy-alpha-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2. (C) 2011 Elsevier Ltd. All rights reserved.
• LAFONT, DOMINIQUE;DESCOTES, GRARD, CARBOHYDR. RES., 175,(1988) N 1, 35-48
  作者：LAFONT, DOMINIQUE、DESCOTES, GRARD

  DOI：——

  日期：——