octyl 2-O-benzoyl-3-O-benzyl-β-D-mannopyranoside | 205869-91-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2-O-benzoyl-3-O-benzyl-β-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-octoxy-4-phenylmethoxyoxan-3-yl] benzoate
• CAS: 205869-91-6
• 化学式: C₂₈H₃₈O₇
• 分子量: 486.606
• InChiKey: REQRQSYJYAUOBP-DNAQHQBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 2-O-benzoyl-3-O-benzyl-β-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 溶剂黄146 、 mercury dibromide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 34.25h， 生成 octyl 6-O-(α-D-mannopyranosyl)-β-D-mannopyranoside
  参考文献：
  名称：

  4,6-di-O-benzoyl-3-O-benzyl-α-d-arabino-hexopyranos-2-ulosyl bromide: A conveniently accessible glycosyl donor for the expedient construction of diantennary β-d-mannosides branched at O-3 and O-6

  摘要：

  A concise practical, large scale-adaptable six-step sequence has been developed for the transformation of diacetone-glucose into 4,6-di-O-benzoyl-3-O-benzyl-alpha-D-arabino-hexo-pyranos-2 -ulosyl bromide (7), a most useful indirect beta-D-mannosyl donor as its blocking group pattern allows the construction of biologically relevant beta-D-mannosides branched at O-3 and O-6. The broad utility of this new ulosyl bromide 7 resides in its high anomeric reactivity, and in the ease and uniformity with which beta-stereocontrol can be achieved over both, glycosidations and carbonyl reduction of the beta-ulosides formed: Koenigs-Knorr conditions exclusively provide beta-glycosiduloses, hydride reduction of their carbonyl functions proceeds with high stereoselectivities (> 20:1) in favor of the beta-D-mannosides, These preparatively auspicious properties are materialized in an efficient, straightforward synthesis of alpha-D-Manp-(1 --> 6)-[alpha-D-Manp-(1 --> 3)]-beta-D-Manp-(1 --> O)-Octyl, the 3,6-O-branched core-mannotrioside carrying an octyl spacer instead of the chitobiosyl unit. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00249-8
• 作为产物：
  描述：

  3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 乙醇 、 4 A molecular sieve 、 Dowex 50 (H⁽¹⁺⁾) 、 氢溴酸 、 sodium methylate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 34.25h， 生成 octyl 2-O-benzoyl-3-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  4,6-di-O-benzoyl-3-O-benzyl-α-d-arabino-hexopyranos-2-ulosyl bromide: A conveniently accessible glycosyl donor for the expedient construction of diantennary β-d-mannosides branched at O-3 and O-6

  摘要：

  A concise practical, large scale-adaptable six-step sequence has been developed for the transformation of diacetone-glucose into 4,6-di-O-benzoyl-3-O-benzyl-alpha-D-arabino-hexo-pyranos-2 -ulosyl bromide (7), a most useful indirect beta-D-mannosyl donor as its blocking group pattern allows the construction of biologically relevant beta-D-mannosides branched at O-3 and O-6. The broad utility of this new ulosyl bromide 7 resides in its high anomeric reactivity, and in the ease and uniformity with which beta-stereocontrol can be achieved over both, glycosidations and carbonyl reduction of the beta-ulosides formed: Koenigs-Knorr conditions exclusively provide beta-glycosiduloses, hydride reduction of their carbonyl functions proceeds with high stereoselectivities (> 20:1) in favor of the beta-D-mannosides, These preparatively auspicious properties are materialized in an efficient, straightforward synthesis of alpha-D-Manp-(1 --> 6)-[alpha-D-Manp-(1 --> 3)]-beta-D-Manp-(1 --> O)-Octyl, the 3,6-O-branched core-mannotrioside carrying an octyl spacer instead of the chitobiosyl unit. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00249-8

文献信息

• 4,6-di-O-benzoyl-3-O-benzyl-α-d-arabino-hexopyranos-2-ulosyl bromide: A conveniently accessible glycosyl donor for the expedient construction of diantennary β-d-mannosides branched at O-3 and O-6
  作者：Frieder W. Lichtenthaler、Ulrich Kläres、Zoltán Szurmai、Bernd Werner

  DOI：10.1016/s0008-6215(97)00249-8

  日期：1997.12

  A concise practical, large scale-adaptable six-step sequence has been developed for the transformation of diacetone-glucose into 4,6-di-O-benzoyl-3-O-benzyl-alpha-D-arabino-hexo-pyranos-2 -ulosyl bromide (7), a most useful indirect beta-D-mannosyl donor as its blocking group pattern allows the construction of biologically relevant beta-D-mannosides branched at O-3 and O-6. The broad utility of this new ulosyl bromide 7 resides in its high anomeric reactivity, and in the ease and uniformity with which beta-stereocontrol can be achieved over both, glycosidations and carbonyl reduction of the beta-ulosides formed: Koenigs-Knorr conditions exclusively provide beta-glycosiduloses, hydride reduction of their carbonyl functions proceeds with high stereoselectivities (> 20:1) in favor of the beta-D-mannosides, These preparatively auspicious properties are materialized in an efficient, straightforward synthesis of alpha-D-Manp-(1 --> 6)-[alpha-D-Manp-(1 --> 3)]-beta-D-Manp-(1 --> O)-Octyl, the 3,6-O-branched core-mannotrioside carrying an octyl spacer instead of the chitobiosyl unit. (C) 1998 Elsevier Science Ltd.