23569-25-7

Upstream product

• 882980-43-0 2-benzyloxy-1-methylpyridinium triflate 
• 768-95-6 1-adamanthanol 
• 100-51-6 benzyl alcohol 
• 7285-83-8 2,4,6-tris(benzyloxy)-1,3,5-triazine 
• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 
• 40864-08-2 2-benzyloxypyridine 
• 768-90-1 1-Adamantyl bromide 

Downstream Products

• 768-95-6 1-adamanthanol 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Preparation of Alkyl Ethers with Diallyltriazinedione-Type Alkylating Agents (ATTACKs-R) Under Acid Catalysis

Diallyltriazinedione-type acid-catalyzed alkylating agents (ATTACKs-R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium-catalyzed intramolecular O-to-N allylic rearrangement of 2,4-bis(allyloxy)-6-chloro-1,3,5-triazine was developed to introduce various alkoxy groups into the N,N′-dialkylated triazinedione skeleton. O-Alkylation of alcohols with ATTACKs-R was carried out in 1,4-dioxane in the presence of 2,6-di-tert-butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs-R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs-R bearing an o-nitro-substituted benzyl group tended to afford low yields. Comparison of four different triazinedione-based benzylating reagents suggested that the N,N′-substituents affected the reactivity.

Development of triazine-based benzylating reagents possessing T-butyl group on the triazine core: Thermally controllable reagents for the initiation of reaction

Benzylating reagents, 4-(4,6-di-t-butyl-1,3,5-triazin-2-yl)-4-benzylmorpholinium triflate, and related derivatives have been developed. The reagents release benzyl triflate as a benzyl cation equivalent upon heating the solution to 40°C under neutral conditions. The O-benzylation of alcohols using a stoichiometric amount of these reagents afforded corresponding benzyl ethers in good to high yields. This was due to the presence of a bulky t-butyl group on the triazine ring of these reagents that prevents the consumption of benzyl triflate via a side reaction with a morpholinotriazine derivative.

Synthesis of Benzyl Alkyl Ethers by Intermolecular Dehydration of Benzyl Alcohol with Aliphatic Alcohols under the Effect of Copper Containing Catalysts

Synthesis of benzyl alkyl ethers was performed in high yields by intermolecular dehydration of benzyl and primary, secondary, tertiary alcohols under the effect of copper containing catalysts. The formation of benzyl alkyl ethers occurs with participation of benzyl cation.

TRIAZINE DIONE COMPOUND

PROBLEM TO BE SOLVED: To provide a novel triazine dione compound useful as an alkylating agent for a nucleophilic compound. SOLUTION: This invention relates to a compound represented by formula (I) [where each symbol is as defined in the specification] and an alkylating agent comprising the compound, and a method for alkylating a nucleophilic compound using the alkylating agent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

N,N′-Dimethylated Benzyloxytriazinedione: A Stable Solid Reagent for Acid-Catalyzed O-Benzylation

N,N′-Dimethylated 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (DMBOT) has been developed as a triazinedione-based, stable solid reagent for acid-catalyzed O-benzylation. The conceptual basis of the design was to fix the core triazinedione skeleton, and

HYDROXY GROUP PROTECTING AGENT AND HYDROXY GROUP PROTECTION METHOD

To provide: a hydroxy group protecting agent which is stable and easy to use, does not have carcinogenicity, a tearing property or the like, and is inexpensive; and a hydroxy group protection method which enables the protection of a hydroxy group under acidic conditions. [Solution] A hydroxy group protecting agent in which at least one protecting group is bound to a nitrogen-containing electron-withdrawing heterocyclic ring through any one of an oxygen atom, a sulfur atom and a nitrogen atom. The heterocyclic ring is a triazine ring or the like, and the protecting group is a benzyl group or the like. Specifically, the hydroxy group protecting agent is 2,4,6-tribenzyloxy-1,3,5-triazine, 2,4,6-tris(4-methoxybenzyloxy)-1,3,5-triazine or the like. In addition, 2,4,6-tris(t-butoxy)-1,3,5-triazine or the like can also be used. For protecting a hydroxy group, a compound of interest which has a hydroxy group is reacted with the hydroxy group protecting agent under acidic conditions.

Development of a new benzylating reagent spontaneously releasing benzyl cation equivalents at room temperature

A new O-benzylating reagent, that is, 4-(4,6-diphenoxy-1,3,5-triazin-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate (DPT-BM), has been developed. Benzyl cation equivalents are generated from DPT-BM by dissolving the compound in a solvent at room tem

Synthesis of 1-adamantyl alkyl ethers by intermolecular dehydration of 1-adamantanol with alcohols catalyzed by copper compounds

Adamantyl alkyl ethers were synthesized in high yields by intermolecular dehydration of 1-adamantanol with alcohols in the presence of copper-containing catalysts.

A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure

Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.