octyl 4-O-acetyl-2-O-benzoyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside | 205869-94-9

• 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 4-O-acetyl-2-O-benzoyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-6)[Bz(-2)][Bn(-3)]Man4Ac(b)-O-octyl；[(2R,3S,4S,5R,6R)-5-acetyloxy-2-octoxy-4-phenylmethoxy-6-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 205869-94-9
• 化学式: C₄₄H₅₈O₁₇
• 分子量: 858.934
• InChiKey: CXCXHCKEDPUONP-REOJLJEMSA-N

物化性质

• 沸点：
  819.5±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  61
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  204
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  octyl 4-O-acetyl-2-O-benzoyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 51.25h， 生成 (2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
  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：

  octyl 2-O-benzoyl-3-O-benzyl-β-D-mannopyranoside 在 吡啶 、 4 A molecular sieve 、 mercury dibromide 作用下， 反应 32.25h， 生成 octyl 4-O-acetyl-2-O-benzoyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-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

文献信息

• Anomalous Zemplén deacylation reactions of α- and β-d-mannopyranoside derivatives
  作者：Károly Ágoston、András Dobó、János Rákó、János Kerékgyártó、Zoltán Szurmai

  DOI：10.1016/s0008-6215(00)00283-4

  日期：2001.1

  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.