甲基 4,6-O-亚苄基-3-O-甲基-alpha-D-吡喃甘露糖苷 | 52260-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 中文名称: 甲基 4,6-O-亚苄基-3-O-甲基-alpha-D-吡喃甘露糖苷
• 中文别名: 甲基4,6-O-亚苄基-3-O-甲基-α-D-甘露吡喃糖苷；4,6-O-亚苄基-1,3-二-O-甲基-Α-D-吡喃甘露糖苷
• 英文名称: methyl 4,6-O-benzylidene-3-O-methyl-α-D-mannopyranoside
• 英文别名: 4,6-O-Benzylidene-1,3-di-O-methyl-a-D-mannopyranoside；(4aR,6S,7S,8R,8aR)-6,8-dimethoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 52260-48-7
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: KCXVHILKGUDBTH-UISBESDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  甲基 4,6-O-亚苄基-3-O-甲基-alpha-D-吡喃甘露糖苷 生成 Methyl 2-O-(3-methoxybenzyl)-3,4,6-tri-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  MARTIN, OLIVIER R.;HENDRICKS, A. V.;DESHPANDE, PRASHANT P.;CUTLER, AMOS B+, CARBOHYDR. RES., 196,(1990) C. 41-58

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-O-methyl-α-D-mannopyranoside 、 苯甲醛二乙缩醛 在 zinc(II) chloride 作用下， 反应 4.0h， 以83%的产率得到甲基 4,6-O-亚苄基-3-O-甲基-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)

  摘要：

  The title compound methyl O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)-[(1 --> 4)- O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)](4)-(1 --> 4)-2,6-di-O-benzyl-3-O-methyl-alpha-D- mannopyranoside (2) was synthesized in a blockwise manner, employing trichloroacetimidate (11) and (20) as glycosyl donors. The strategy relies on the single-step preparation of the 3-O-methyl ethers (4) and (12) as starting materials. Since all intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy using the methyl proton signals, Compound 2 corresponds to the reducing terminal hexasaccharide of mycobacterial 3-O-methylmannose polysaccharide (MMP). MMP has the unusual property of stimulating the fatty acid synthetase multienzyme complex. Compound 2 can serve as a suitable glycosyl acceptor for the synthesis of extended fragments of MMP. (C) 1996 Elsevier Science-Ltd.

  DOI：

  10.1016/s0008-6215(96)00239-x

文献信息

• Synthesis of C-glycosylarenes by way of internal reactions of benzylated and benzoylated carbohydrate derivatives
  作者：Olivier R. Martin、Carmen A.V. Hendricks、Prashant P. Deshpande、Amos B. Cutler、Stefanie A. Kane、Sunkada P. Rao

  DOI：10.1016/0008-6215(90)84105-4

  日期：1990.2

  "Internal" C-glycosylarenes [e.g., (2R,3S,3aS,9bR)-3,3a,5,9b-tetrahydro-3-methoxy- and -3,7-dimethoxy-2-methoxymethyl-2H-furo[3,2-c][2]benzopyran] were prepared by intramolecular reactions of 2-O-benzyl derivatives of methyl 3,5-di-O-methyl-D-xylofuranoside (2) and their conversion into authentic C-glycosylated aromatic systems was investigated. The auxiliary benzylic linkage could not be cleaved by

  “内部” C-糖基芳烃[例如，（2R，3S，3aS，9bR）-3,3a，5,9b-四氢-3-甲氧基-和-3,7-二甲氧基-2-甲氧基甲基-2H-呋喃[3 ，2-c] [2]苯并吡喃]是通过3,5-二-O-甲基-D-木呋喃糖苷（2）的2-O-苄基衍生物的分子内反应制备的，并将其转化为真正的C-糖基化芳族体系被调查了。氢解不能裂解辅助的苄基键；在这些条件下获得异色烷衍生物（例如，（3S）-3,4-二氢-3-[（1R，2R）-2-羟基-1,3-二甲氧基丙基] -5-甲氧基xy-1H-2-苯并吡喃）条件。但是，用四氧化钌氧化伯苄基位置可得到相应的内酯（二氢异香豆素衍生物，例如（2R，3S，3aS，9bR）-2,3,3a，9b-四氢-3,7-二甲氧基-2-甲氧基-甲基-5H-呋喃[3，2-c] [2]苯并吡喃-5-酮）可通过皂化作用打开，从而产生立体化学上独特的C-糖基苯甲酸衍生物。相同类型的内酯直
• Synthesis of Methyl<i>O</i>-<i>α</i>-D-Mannosyl-(1→4)-[(3-<i>O</i>-methyl-<i>α</i>-D- mannosyl)-(1→4)-]_<i>n</i>3-<i>O</i>-methyl-<i>α</i>-D-mannosides (<i>n</i>= 0, 1, and 2) via Dehydrative Glycosylation
  作者：Motoko Hirooka、Megumi Terayama、Emi Mitani、Shinkiti Koto、Asako Miura、Kayo Chiba、Ayano Takabatake、Takako Tashiro

  DOI：10.1246/bcsj.75.1301

  日期：2002.6

  Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.

  通过脱水糖基化反应合成了甲基 O-α-D-吡喃甘露糖基-(1→4)-[(3-O-甲基-α-D-吡喃甘露糖基-(1→4)-]n3-O-甲基-α-D-吡喃甘露糖苷（n = 0、1 和 2），这是分枝杆菌中 3-O-甲基甘露糖多糖（MMP）的最低同源物。由对硝基苯磺酰氯、三氟甲磺酸银和三乙胺，对硝基苯磺酰氯、三氟甲磺酸银和 1，8-二氮杂双环[5.4.0]十一-7-烯，以及三氟甲磺酸三甲基硅酯和吡啶组成的试剂体系非常有用。
• Improved synthesis of 2-deoxy-2-fluoro-D-glucose using fluoride ion.
  作者：TERUSHI HARADAHIRA、MINORU MAEDA、YASUNOBU KAI、HIROKO OMAE、MASAHARU KOJIMA

  DOI：10.1248/cpb.33.165

  日期：——

  Methyl 3-O-benzyl-4, 6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-mannopyranoside (7) was examined as a substrate for the preparation of 2-deoxy-2-fluoro-D-glucose (1) by fluoride ion treatment. The triflate (7) reacted rapidly with tetraalkylammonium fluorides in acetonitrile or tetrahydrofuran to give methyl 3-O-benzyl-4, 6-O-benzylidene-2-deoxy-2-fluoro-β-D-glucopyranoside (10) in 52-57% yield. Removal of the protecting groups from 10 by the use of 50% methanesulfonic acid afforded the required 1 in good yield. This synthetic sequence may provide an effective alternative to known methods for preparing 18F-labeled 1.

  研究人员将 3-O-苄基-4，6-O-亚苄基-2-O-(三氟甲磺酰基)-β-D-吡喃甘露糖苷（7）作为底物，通过氟离子处理制备 2-脱氧-2-氟-D-葡萄糖（1）。三酸酯（7）与四烷基氟化铵在乙腈或四氢呋喃中迅速反应，得到甲基 3-O-苄基-4，6-O-亚苄基-2-脱氧-2-氟-β-D-吡喃葡萄糖苷（10），收率为 52-57%。用 50%的甲磺酸去除 10 中的保护基团，可以得到所需的 1，收率很高。这种合成方法可以有效替代已知的 18F 标记 1 的制备方法。
• Synthesis of Monomethyl Derivatives of<i>P</i>-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases
  作者：Wataru Hakamata、Toshiyuki Nishio、Reiko Sato、Takahiro Mochizuki、Kazuya Tsuchiya、Maki Yasuda、Tadatake Oku

  DOI：10.1080/07328300008544084

  日期：2000.1

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.