2,3,4-tri-O-acetyl-6-amino-1,6-anhydro-6-deoxy-β-D-galactopyranose | 215661-94-2

• 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: 2,3,4-tri-O-acetyl-6-amino-1,6-anhydro-6-deoxy-β-D-galactopyranose
• CAS: 215661-94-2
• 化学式: C₁₂H₁₇NO₇
• 分子量: 287.269
• InChiKey: QUOPWYDIOCZEEK-YBXAARCKSA-N

物化性质

• 沸点：
  353.695±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.330±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-amino-1,6-anhydro-6-deoxy-β-D-galactopyranose 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以98%的产率得到Acetic acid (3S,4R,5S,6R)-3,5-diacetoxy-6-hydroxy-azepan-4-yl ester
  参考文献：
  名称：

  Efficient synthesis of seven-membered iminocyclitols from glycosylenamines

  摘要：

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00649-8
• 作为产物：
  描述：

  2-[((2R,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-methanesulfonyloxymethyl-tetrahydro-pyran-2-ylamino)-methylene]-malonic acid diethyl ester 在 sodium methylate 、 氯 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-acetyl-6-amino-1,6-anhydro-6-deoxy-β-D-galactopyranose
  参考文献：
  名称：

  Efficient synthesis of seven-membered iminocyclitols from glycosylenamines

  摘要：

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00649-8

文献信息

• Synthesis of 6-amino-1,6-anhydro-6-deoxysugar derivatives
  作者：Dominique Lafont、Andreas Wollny、Paul Boullanger

  DOI：10.1016/s0008-6215(98)00089-5

  日期：1998.8

  lphosphonioamino- β - d -glycopyranose salts thus obtained were transformed into the corresponding 2,3,4-tri- O -acetyl-6-amino-1,6-anhydro-6-deoxy- β - d -glycopyranoses which were further N -acylated or N -alkoxycarbonylated. 1 H and 13 C NMR of these products show the occurrence of two rotamers in solution, due to restricted rotations around the amide bond.

  摘要三苯基膦与2,3,4-三-O-乙酰基-6-O-对甲苯磺酰基-β-d-糖基叠氮基叠氮化物的斯托丁格反应导致了端基异亚氨基正膦，该异位亚氨基正膦通过消除C-6处的磺酸盐而原位重排。将如此获得的1，6-脱水-6-脱氧-6-三苯基膦酰氨基-β-d-甘露糖盐转化为相应的2,3,4-三-O-乙酰基-6-氨基-1,6-脱水-盐。进一步被N-酰化或N-烷氧基羰基化的6-脱氧-β-d-甘露聚糖。这些产物的1 H和13 C NMR表明，由于酰胺键周围的旋转受限，在溶液中存在两个旋转异构体。