methyl 2,3-di-O-benzyl-6-O-(2-naphthyl)methyl-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-O-(2-naphthyl)methyl-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-6-methoxy-2-(naphthalen-2-ylmethoxymethyl)-4,5-bis(phenylmethoxy)oxan-3-ol
• 化学式: C₃₂H₃₄O₆
• 分子量: 514.618
• InChiKey: XDMGXEXOHFWNTE-MQSWGENCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 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 methyl 2,3-di-O-benzyl-6-O-(2-naphthyl)methyl-α-D-galactopyranoside
  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

• Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ
  作者：Joseph A Wright、Jinquan Yu、Jonathan B Spencer

  DOI：10.1016/s0040-4039(01)00563-9

  日期：2001.6

  The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups. (C) 2001 Elsevier Science 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.