benzyl 2,3-di-O-benzyl-6-O-tosyl-β-D-glucopyranoside | 74352-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-di-O-benzyl-6-O-tosyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3-hydroxy-4,5,6-tris(phenylmethoxy)oxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 74352-49-1
• 化学式: C₃₄H₃₆O₈S
• 分子量: 604.721
• InChiKey: KSKBZRHRIBJZJD-BGSSSCFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-di-O-benzyl-6-O-tosyl-β-D-glucopyranoside 在 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 氢气 、 sodium acetate 、 silver trifluoromethanesulfonate 、 三乙胺 、 对硝基苯磺酰氯 、 palladium dichloride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 34.83h， 生成 O-(6-deoxy-α-D-galactopyranosyl)-(1->4)-6-deoxy-D-glucopyranose
  参考文献：
  名称：

  In situ Activating Glycosylation of 6-Deoxysugars: Synthesis ofO-α-D-Fucosyl-(1→4)-O-α-D-fucosyl-(1→4)-O-α-D-quinovosyl-(1→4)-D-quinovose

  摘要：

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。

  DOI：

  10.1246/bcsj.73.967
• 作为产物：
  描述：

  benzyl 4,6-O-benzylidene-β-D-glucopyranoside 在 氢氧化钾 作用下， 以 吡啶 为溶剂， 反应 73.3h， 生成 benzyl 2,3-di-O-benzyl-6-O-tosyl-β-D-glucopyranoside
  参考文献：
  名称：

  In situ Activating Glycosylation of 6-Deoxysugars: Synthesis ofO-α-D-Fucosyl-(1→4)-O-α-D-fucosyl-(1→4)-O-α-D-quinovosyl-(1→4)-D-quinovose

  摘要：

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。

  DOI：

  10.1246/bcsj.73.967

文献信息

• A convenient etherification of the primary hydroxyl group of glucopyranosides
  作者：Jean-Michel Petit、Jean-Claude Jacquinet、Pierre Sinaÿ

  DOI：10.1016/s0008-6215(00)85527-5

  日期：1980.6
• Probing the active-site requirements of human intestinal N-terminal maltase glucoamylase: The effect of replacing the sulfate moiety by a methyl ether in ponkoranol, a naturally occurring α-glucosidase inhibitor
  作者：Razieh Eskandari、Kyra Jones、David R. Rose、B. Mario Pinto

  DOI：10.1016/j.bmcl.2010.08.020

  日期：2010.10

  Ponkoranol is a naturally occurring glucosidase inhibitor isolated from the plant Salacia reticulata. The compound comprises a sulfonium ion with an internal sulfate counter ion. We report here an efficient synthetic route to 3'-O-methyl ponkoranol to test the hypothesis that occupation of a hydrophobic pocket by a methyl group instead of the polar sulfate ion within the active site of human N-terminal maltase glucoamylase would be beneficial. The synthetic strategy relies on the nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D-arabinitol at the C-6 position of benzyl 6-O-p-toluenesulfonyl beta-D-glucopyranoside, followed by deprotection using boron trichloride and reduction with sodium borohydride. The target compound inhibited the N-terminal catalytic domain of intestinal human maltase glucoamylase (ntMGAM) with a K-i value of 0.50 +/- 0.04 mu M, higher than those of de-O-sulfonated ponkoranol (K-i = 43 +/- 3 nM), or its 5'-stereoisomer (K-i = 15 +/- 1 nM). We conclude that the interaction of the methyl group with hydrophobic residues in the active site is not as beneficial to inhibition of ntMGAM as the other interactions of the polyhydroxylated chain with active-site residues. (C) 2010 Elsevier Ltd. All rights reserved.
• In situ Activating Glycosylation of 6-Deoxysugars: Synthesis of<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-Fucosyl-(1→4)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-fucosyl-(1→4)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-quinovosyl-(1→4)-<b>D</b>-quinovose
  作者：Shinkiti Koto、Ami Kusunoki、Motoko Hirooka

  DOI：10.1246/bcsj.73.967

  日期：2000.4

  The linear tetrasaccharide, α-D-fucopyranosyl-(1→4)-α-D-fucopyranosyl-(1→4)-α-D-quinovopyranosyl-(1→4)-D-quinovopyranose, the sugar cluster of asterosaponin A from the starfish, Asterias amurensis, was synthesized in a convergent manner. We employed an in situ activating glycosylation using 1-OH sugar derivatives and a system of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine as well as a related system.

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。