1-methylethyl 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-β-D-glucopyranoside | 130259-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methylethyl 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-β-D-glucopyranoside
• 英文别名: isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(methoxycarbonylamino)-6-propan-2-yloxyoxan-2-yl]methyl acetate
• CAS: 130259-39-1
• 化学式: C₁₇H₂₇NO₁₀
• 分子量: 405.402
• InChiKey: QKTCFTSHWBSGHH-OXGONZEZSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  494.6±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-methylethyl 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-β-D-glucopyranoside 在 吡啶 、 甲基三氯硅烷 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 异丙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  The Mild Cleavage of 2-Amino-2-deoxy-d-glucoside Methoxycarbonyl Derivatives

  摘要：

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.

  DOI：

  10.1021/ol0063353
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate 在 silver trifluoromethanesulfonate 4 A molecular sieve 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 37.0h， 生成 1-methylethyl 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-β-D-glucopyranoside
  参考文献：
  名称：

  The Mild Cleavage of 2-Amino-2-deoxy-d-glucoside Methoxycarbonyl Derivatives

  摘要：

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.

  DOI：

  10.1021/ol0063353

文献信息

• The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-d-glucose as donors in glycosylation reactions
  作者：Paul Boullanger、Martine Jouineau、Boufelja Bouammali、Dominique Lafont、Gérard Descotes

  DOI：10.1016/0008-6215(90)84077-8

  日期：1990.7

  6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-alpha-D-glucopyra nosyl bromides have been used as donors in glycosylation reactions with model alcohols. beta-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation

  1,3,4,6-四-O-乙酰基-2-烷氧基羰基氨基-2-脱氧-β-D-glu复制糖和3,4,6-三-O-乙酰基-2-烷氧基羰基氨基-2-脱氧-α在与模型醇的糖基化反应中，已将-D-吡喃葡萄糖烷基溴用作供体。β-糖苷以高收率和高度的1，2-反式立体选择性获得。恶唑烷酮是一些吡喃葡萄糖基溴化物与低反应性醇反应形成的主要产物，但所有产物的形成都可以通过烷氧基羰基氨基的强烈参与来解释。
• BOULLANGER, PAUL;JOUINEAU, MARTINE;BOUAMMALI, BOUFELJA;LAFONT, DOMINIQUE;+, CARBOHYDR. RES., 202,(1990) C. 151-164
  作者：BOULLANGER, PAUL、JOUINEAU, MARTINE、BOUAMMALI, BOUFELJA、LAFONT, DOMINIQUE、+

  DOI：——

  日期：——