methyl 3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside | 107937-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside
• 英文别名: 3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside；(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(2S,3S,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 107937-20-2
• 化学式: C₃₄H₄₂O₁₁
• 分子量: 626.701
• InChiKey: VPXQMHKBUFFVLI-AWRYZPBRSA-N

物化性质

• 沸点：
  771.7±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  145.53
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 以93%的产率得到а1,2-单甘露醇,а甲基糖苷
  参考文献：
  名称：

  Lysosomal-enzyme targeting: the phosphorylation of synthetic d-mannosyl saccharides by UDP-N-acetylglucosamine:lysosomal-enzyme N-acetylglucosaminephosphotransferase from rat-liver microsomes and fibroblasts

  摘要：

  Phosphorylation of the D-mannose residues of lysosomal enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes. The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes. To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides. Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy. Of all the D-mannosyl saccharides tested, alpha-D-Man-(1----2)-alpha-D-Man-(1----OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.

  DOI：

  10.1016/s0008-6215(00)90298-2
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 methyl 3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  Lysosomal-enzyme targeting: the phosphorylation of synthetic d-mannosyl saccharides by UDP-N-acetylglucosamine:lysosomal-enzyme N-acetylglucosaminephosphotransferase from rat-liver microsomes and fibroblasts

  摘要：

  Phosphorylation of the D-mannose residues of lysosomal enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes. The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes. To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides. Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy. Of all the D-mannosyl saccharides tested, alpha-D-Man-(1----2)-alpha-D-Man-(1----OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.

  DOI：

  10.1016/s0008-6215(00)90298-2

文献信息

• Synthesis of some monodeoxyfluorinated methyl and 4-nitrophenyl α-d-mannobiosides and a related 4-nitrophenyl α-d-mannotrioside
  作者：Shaheer H. Khan、Rakesh K. Jain、Saeed A. Abbas、Khushi L. Matta

  DOI：10.1016/0008-6215(90)84297-8

  日期：1990.5

  of diol 18 with 20 gave 4-nitrophenyl 4-O-acetyl-6-deoxy-6-fluoro-3-O- (21) and -2-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D- mannopyranoside (23) in the ratio of approximately 2:1, together with a small proportion of a branched trisaccharide. 4-Nitrophenyl 4,6-di-O-acetyl-alpha-D-mannopyranoside was similarly glycosylated with bromide 19 to give 4-nitrophenyl 4,6-di-O-acetyl-3-O- and

  用N，N-二乙基氨基硫磺处理甲基3,4,6-三-O-苄基-2-O-（2,3,4-三-O-乙酰基-α-D-甘露吡喃糖基）-α-D-甘露吡喃糖苷三氟化物（Et2NSF3），然后进行O-脱乙酰化和催化氢解，得到甲基2-O-（6-脱氧-6-氟-α-D-甘露吡喃糖基）-α-D-甘露吡喃糖苷（8）。甲基6-脱氧-6-氟-2-O-α-D-甘露吡喃糖基-α-D-甘露吡喃糖苷（11）类似地从甲基3-O-苄基-2-O-（2,3,4,6 -四-O-乙酰基-α-D-甘露吡喃糖基-α-D-甘露吡喃糖苷1,2,3,4-四-O-乙酰基-6-脱氧-6-氟-β-D-甘露吡喃糖（13），通过处理1,2,3,4-四-O-乙酰基-β-D-甘露吡喃糖获得用于合成8和11的4-硝基苯基类似物及其3-O-连接的异构体的化合物用Et2NSF3在氯化锡（IV）存在下用4-硝基苯酚处理13 然后依次进行O-脱乙酰基，异丙基化，乙酰化和缩醛基
• Synthesis of methyl 2-O- and 3-O-α-d-talopyranosyl-α-d-mannopyranoside
  作者：Surjit S. Rana、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)90299-4

  日期：1986.9

  borohydride, converted 2 into methyl 3,4,6-tri-O-benzyl-2-O-[6-O-(tert-butyldiphenylsilyl)-2,3-O-isopro pylidene- alpha-D-talopyranosyl]-alpha-D-mannopyranoside (5). Treatment of 5 with a molar solution of tetrabutylammonium fluoride in dry oxolane produced a diol which, on O-de-isopropylidenation followed by catalytic hydrogenolysis, afforded the disaccharide glycoside methyl 2-O-alpha-D-talopyranosyl

  通过处理甲基3，合成了3,4,6-三-O-苄基-2-O- [6-O-（叔丁基二苯基甲硅烷基）-α-D-甘露吡喃糖基]-α-D-甘露吡喃糖苷（2）在咪唑存在下，将4,6-三-O-苄基-2-O-α-D-甘露吡喃糖基-α-D-甘露吡喃糖苷与叔丁基氯二苯基硅烷一起使用。异亚丙基化，然后用氯铬酸吡啶鎓氧化，再用硼氢化钠进行立体选择性还原，将2转化为甲基3,4,6-三-O-苄基-2-O- [6-O-（叔丁基二苯基甲硅烷基）-2,3 -O-异丙基亚吡啶-α-D-塔拉吡喃糖基]-α-D-甘露吡喃糖苷（5）。用氟化四丁基铵在干燥的环氧丙烷中的摩尔溶液处理5，得到二醇，其在O-去异亚丙基化之后，通过催化氢解，得到二糖苷甲基2-O-α-D-塔吡喃糖基-α-D-甘露吡喃糖苷。甲基3-O-α-D-talopyranosyl-α-D-甘露吡喃糖苷的合成通过类似的反应顺序完成。最终的二糖和各种其他中间体的结构是通过1H-和13C-nmr光谱确定的。
• Synthesis of some d-mannosyl-disaccharides containing D-mannose 6-phosphate residues
  作者：Khushi L. Matta、Manjit S. Chowdhary、Rakesh K. Jain、Saeed A. Abbas

  DOI：10.1016/0008-6215(86)80026-x

  日期：1986.8