octyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-mannopyranoside | 205869-95-0

• 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 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-mannopyranoside
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-3)[Bz(-2)][Bz(-4)][Bz(-6)]Man(b)-O-octyl；[(2R,3R,4S,5S,6R)-3,5-dibenzoyloxy-6-octoxy-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 205869-95-0
• 化学式: C₄₉H₅₈O₁₈
• 分子量: 934.989
• InChiKey: SVZUOGADYPMRTI-DOXKWXMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  octyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以80%的产率得到octyl α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-mannopyranoside
  参考文献：
  名称：

  Anomalous Zemplén deacylation reactions of α- and β-d-mannopyranoside derivatives

  摘要：

  Reaction of mono-, di-, and trisaccharide derivatives of methyl beta -D- and octyl beta -D-mannopyranosides bearing ester groups at isolated and non-isolated positions on the same molecule, under Zemplen conditions (catalytic amount of sodium methoxide in methanol) gave partially deacylated compounds, in which the O-acyl groups were retained at isolated sites. In the case of one disaccharide, all the benzoyl groups remained intact at the reducing end, while all the acetyl functions were removable from the nonreducing end. In another case, both isolated ester groups at positions 2 and 4 were retained at the reducing end. The isolated 2-O-acyl groups on methyl alpha -D-mannopyranoside compounds were more labile than on the corresponding beta -mannosides under the same conditions. The mechanism of the reaction may be different for ester groups at isolated or non-isolated positions. In the latter case, acyl migration may take place and carry acyl groups into a less hindered position. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00283-4
• 作为产物：
  描述：

  3-O-benzyl-D-glucopyranose 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 乙醇 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢溴酸 、 氢气 、 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 为溶剂， 反应 173.0h， 生成 octyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-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