2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-D-mannopyranozyl trichloroacetimidate | 484647-42-9

• 英文名称: 2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-D-mannopyranozyl trichloroacetimidate
• 英文别名: Bn(-3)[Bn(-4)][TBDMS(-6)]Man2Ac-O-C(NH)CCl3；[(3S,4S,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-bis(phenylmethoxy)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 484647-42-9
• 化学式: C₃₀H₄₀Cl₃NO₇Si
• 分子量: 661.095
• InChiKey: ZKHMYCZALXUSGA-HKQFDGPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-D-mannopyranozyl trichloroacetimidate 、 benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside
  参考文献：
  名称：

  Total Synthesis of Desferrisalmycin B

  摘要：

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

  DOI：

  10.1021/ja028386w
• 作为产物：
  描述：

  1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 在 咪唑 、 Dowex resin 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-D-mannopyranozyl trichloroacetimidate
  参考文献：
  名称：

  Total Synthesis of Desferrisalmycin B

  摘要：

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

  DOI：

  10.1021/ja028386w