p-methoxyphenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-β-D-glucopyranoside | 473553-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-3-(naphthalen-2-ylmethoxy)-4,5-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 473553-53-6
• 化学式: C₃₈H₃₈O₇
• 分子量: 606.716
• InChiKey: ATJBMNSQNPBWCS-JTDOPDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-β-D-glucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 p-methoxyphenyl 2,3-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers

  摘要：

  alpha-, beta-D-Gluco-, galacto-, 2-deoxy-2-phthalimido-beta-D-glucopyranosides with different aglycons (methyl, allyl, p-methoxyphenyl, thioethyl) reacted with 2-naphthaldehyde dimethyl acetal to give rise to 4,6-O-(2-naphthyl)methylene acetals. The acetals were converted into fully protected compounds bearing benzoyl, benzyl, allyl, p-methoxybenzyl groups. The fully alkylated dioxane-type acetals were hydrogenolysed with AlH3 (3LiAlH(4)-AlCl3) reagent to furnish 4-O-NAP/6-OH derivatives. All acetals were treated with BH3.Me3N-AlCl3 in THF and a reverse regioselectivity was observed, producing 6-O-NAP/4-OH derivatives. Similar regioselectivity was also observed by using NaCNBH3-HCl reagent. In all reactions very mild reaction conditions were required, regioselectivity was better than 93:7, and the isolated yields were between 83-92%. All compounds were characterised by H-1 and C-13 NMR spectra. Solid-state and solution conformation of methyl 2,3-di-O-acetyl-4,6-O-(2-naphthyl)methylene-a-D-galactopyranoside were elucidated by X-ray and NMR measurements. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00515-x
• 作为产物：
  描述：

  4-甲氧基苯基Β-D-吡喃葡萄糖苷 在 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 p-methoxyphenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers

  摘要：

  alpha-, beta-D-Gluco-, galacto-, 2-deoxy-2-phthalimido-beta-D-glucopyranosides with different aglycons (methyl, allyl, p-methoxyphenyl, thioethyl) reacted with 2-naphthaldehyde dimethyl acetal to give rise to 4,6-O-(2-naphthyl)methylene acetals. The acetals were converted into fully protected compounds bearing benzoyl, benzyl, allyl, p-methoxybenzyl groups. The fully alkylated dioxane-type acetals were hydrogenolysed with AlH3 (3LiAlH(4)-AlCl3) reagent to furnish 4-O-NAP/6-OH derivatives. All acetals were treated with BH3.Me3N-AlCl3 in THF and a reverse regioselectivity was observed, producing 6-O-NAP/4-OH derivatives. Similar regioselectivity was also observed by using NaCNBH3-HCl reagent. In all reactions very mild reaction conditions were required, regioselectivity was better than 93:7, and the isolated yields were between 83-92%. All compounds were characterised by H-1 and C-13 NMR spectra. Solid-state and solution conformation of methyl 2,3-di-O-acetyl-4,6-O-(2-naphthyl)methylene-a-D-galactopyranoside were elucidated by X-ray and NMR measurements. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00515-x

文献信息

• Selective removal of the (2-naphthyl)methyl protecting group in the presence of p-methoxybenzyl group by catalytic hydrogenation
  作者：László Lázár、Lóránt Jánossy、Magdolna Csávás、Mihály Herczeg、Anikó Borbása、Sándor Antus

  DOI：10.3998/ark.5550190.0013.526

  日期：——

  Selective cleavage of the (2-naphthyl)methyl (NAP) group in the presence of p-methoxybenzyl (PMB), benzyl and benzylidene groups was achieved by catalytic hydrogenation with a series of monosaccharides. At a disaccharide level, the PMB group was stable upon hydrogenolysis of the NAP, however, partial cleavage of benzyl ether functions was observed.

  在对甲氧基苄基 (PMB)、苄基和亚苄基存在下，(2-萘基)甲基 (NAP) 基团的选择性裂解是通过一系列单糖的催化氢化实现的。在二糖水平上，PMB 基团在 NAP 氢解时是稳定的，但是，观察到苄基醚功能的部分裂解。
• Synthesis of sulfonic acid-containing maltose-type keto-oligosaccharides by an iterative approach
  作者：Gábor Májer、Magdolna Csávás、László Lázár、Mihály Herczeg、Atttila Bényei、Sándor Antus、Anikó Borbás

  DOI：10.1016/j.tet.2012.04.067

  日期：2012.6

  Two different series of (2 -> 5)-alpha-linked homologous keto-oligosaccharides up to tri- and tetrasaccharide were synthesized by an iterative approach, using 3,4,7-tri-O-benzyl-5-O-(2-naphthyl)methyl-1-deoxy-1-ethoxysulfonyl-alpha-D-gluco-hept-2-ulopyranosyl chloride as a key building block. An iterative cycle consisted of a glycosylation step followed by selective cleavage of the (2-naphthyl)methyl group. (C) 2012 Elsevier Ltd. All rights reserved.
• Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers
  作者：Anikó Borbás、Zoltán B Szabó、László Szilágyi、Attila Bényei、András Lipták

  DOI：10.1016/s0040-4020(02)00515-x

  日期：2002.7

  alpha-, beta-D-Gluco-, galacto-, 2-deoxy-2-phthalimido-beta-D-glucopyranosides with different aglycons (methyl, allyl, p-methoxyphenyl, thioethyl) reacted with 2-naphthaldehyde dimethyl acetal to give rise to 4,6-O-(2-naphthyl)methylene acetals. The acetals were converted into fully protected compounds bearing benzoyl, benzyl, allyl, p-methoxybenzyl groups. The fully alkylated dioxane-type acetals were hydrogenolysed with AlH3 (3LiAlH(4)-AlCl3) reagent to furnish 4-O-NAP/6-OH derivatives. All acetals were treated with BH3.Me3N-AlCl3 in THF and a reverse regioselectivity was observed, producing 6-O-NAP/4-OH derivatives. Similar regioselectivity was also observed by using NaCNBH3-HCl reagent. In all reactions very mild reaction conditions were required, regioselectivity was better than 93:7, and the isolated yields were between 83-92%. All compounds were characterised by H-1 and C-13 NMR spectra. Solid-state and solution conformation of methyl 2,3-di-O-acetyl-4,6-O-(2-naphthyl)methylene-a-D-galactopyranoside were elucidated by X-ray and NMR measurements. (C) 2002 Elsevier Science Ltd. All rights reserved.