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정봉영,심영기,Chung Bong Young,Sim Young Key Korean Chemical Society 1979 대한화학회지 Vol.23 No.1
Silver triflate와 syn-collidine 존재하에서 3,4,6-tri-O-acetyl-2-phthalimido-${\beta}$-D-glucopyranosyl bromide (2)와 1,2;3,4-di-O-isopropylidene-${\alpha}$-D-galactopyranose (3)를 반응시켜 1,2;3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-${\beta}$-D-glucopyranosyl)-${\alpha}$-D-galactopyranose (4)를 $86{\%}$의 수득률로 얻었다. 화합물 4를 hydrazine과 작용시켜 phthalimido기와 acetyl기를 동시에 제거한후, 다시 acetyl화하고 isopropylidene기와 O-acetyl기를 가수분해하면 6-O-(2-acetamido-2-deoxy-${\beta}$-D-glucopyranosyl)-D-galactopyranose (1)가 총수득율 $65.8{\%}$로 얻어졌다. 또한 화합물 4를 변형시켜 특정위치에 hydroxyl기를 가진 몇 가지 유도체도 합성하였다. Condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-${\beta}$-D-glucopyranosyl bromide (2) with 1,2;3,4-di-O-isopropylidene-${\alpha}$-D-galactopyranose (3) in the presence of silver triflate and syn-collidine gave 1,2;3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-${\beta}$-D-glucopyranosyl)-${\alpha}$-D-galactopyranose (4) in $86{\%}$ yield. Cleavage of phthalimido group and de-O-acetylation with hydrazine, acetylation, and hydrolysis of isopropylidene and O-acetyl groups furnished 6-O-(2-acetamido-2-deoxy-${\beta}$-D-glucopyranosyl)-D-galactopyranose (1) with overall yield of $65.8{\%}$ starting from 3. Some other derivatives of 1 which have free hydroxyl groups at the specific position have also been prepared from 4. These compounds could be used as precursors for further glycosidation reactions.
1,4-디클로로-1,4-디메톡시부탄올 이용한 카르바졸의 합성
정봉영,배덕종,진정일,이승달,Chung Bong Young,Duck Jong Bae,xJung-Il 배덕종,Seung Dal Lee 대한화학회 1992 대한화학회지 Vol.36 No.4
1,4-Dichloro-1,4-dimethoxybutane과 일차 아민 또는 아미드를 약 염기성인 Amberlyst A-21 resin 존재하에서 반응시켜 N-치환된 피롤을 합성하였으며, 이 피롤 화합물에 1,4-dichloro-1,4-dimethoxybutane를 다시 반응시켜 N-치환된 카르바졸을 합성하였다. N-Substituted pyrroles were synthesized from 1,4-dichloro-1,4-dimethoxybutane and primary amines or amide in the presence of Amberlyst A-21 resin. Further reation of these N-substituted pyrroles with 1,4-dichloro-1,4-dimethoxybutane gave N-substituted carbazoles in moderate yields.
정봉영,김영환,Chung Bong Young,Kim Young-Hwan Korean Chemical Society 1979 대한화학회지 Vol.23 No.3
Phthalimido기와 2,2,2-trichloroethyl기는 acetic acid와 같은 산성용매에서 zine dust에 의하여 각각 3-hydroxyphthalimidino기로 환원 되거나 혹은 환원분해된다. 그러나 THF-pH 4.5 buffer 혼합용매를 사용하므로써, free carboxylic acid가 존재하지 않는 경우, phthalimido는 환원시키지 않고 2,2,2-trichloroethyl기만을 선택적으로 환원분해시킬 수 있음을 발견하였다. 따라서 $2,2,2-trichloroethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-{\beta}-D-glucopyranose$ (1)를 THF-pH 4.5 butter 혼합용매에서 zinc dust와 반응시키면, 2,2,2-trichloroethyl 기만이 선택적으로 환원분해된 $3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-{\beta}-D-glucopyranose$ (5)를 좋은 수득율로 얻을 수 있었다. In acidic media such as aqueous acetic acid, phthalimide is reduced with zinc dust to give 3-hydroxyphthalimidine while the 2,2,2-trichloroethyl esters or glycosides are reductively cleaved. However, it has been discovered that, by employing a mixture of THF and pH 4.5 buffer solution as a solvent, 2,2,2-trichloroethyl group can be selectively removed with activated zinc dust in the presence of phthalimido function, provided that the reactant or the product does not have any free carboxylic acid function. By applying the above methods, reaction of $2,2,2-trichloroethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-{\beta}-D-glucopyranoside$ (1) with activated zinc dust gave a good yield of $3,4, 6-tri-O-acetyl-2-deoxy-2-phthalimido-{\beta}-D-glucopyranose$ (5) in THF-buffer solution, and $3,4,6-tri-O-acetyl-2-deoxy-2-(3-hydroxyphthalimidino)-{\beta}-D-glucopyranose$ (6) in aqueous acetic acid.
A New Route to Diethyl 3,4,5-Trimethoxybenzylmalonate, a Trimethoprim Intermediate
정봉영,이채호,Bong Young Chung,Chae Ho Lee Korean Chemical Society 1985 대한화학회지 Vol.29 No.5
3,4,5-trimethoxybenzoyl chloride와 diethyl malonate를 축합시킨 후, 염소화반응 및 가수소화 분해 반응을 거쳐 diethyl 3,4,5-trimethoxybenzylmalonate를 70%의 수득율로 합성하였다. Direct condensation of 3,4,5-trimethoxybenzoyl chloride with diethyl malonate followed by chlorination and hydrogenolysis afforded diethyl 3,4,5-trimethoxybenzylmalonate in 70% overall yield.