CAJ | 학술논문

首次报道了采用硫代糖法合成熊果苷.葡萄糖经过乙酰化、硫代、脱乙酰基和苯甲酰化反应,转变成供体异丙基-2,3,4,6-四-O-苯甲酰基-1-硫-β-D-葡萄糖苷.对苯二酚选择性地酯化成两种受体对苯二酚单乙酸酯、对苯二酚单苯甲酸酯以及相应的对苯二酚双酯副产物.供体分别与两种受体偶联,由于C-2苯甲酰基的强邻基参与效应,立体专一性地合成了两种保护的熊果苷,后者分别脱保护得到熊果苷.所有产品通过熔点和 1HNMR 等方法进行了结构表征.此外,上述双酯副产物通过选择性地脱酰基,获得了两种可用的受体对苯二酚单酯,有效地得到回收利用.
수차보도료채용류대당법합성웅과감.포도당경과을선화、류대、탈을선기화분갑선화반응,전변성공체이병기-2,3,4,6-사-O-분갑선기-1-류-β-D-포도당감.대분이분선택성지지화성량충수체대분이분단을산지、대분이분단분갑산지이급상응적대분이분쌍지부산물.공체분별여량충수체우련,유우C-2분갑선기적강린기삼여효응,입체전일성지합성료량충보호적웅과감,후자분별탈보호득도웅과감.소유산품통과용점화 1HNMR 등방법진행료결구표정.차외,상술쌍지부산물통과선택성지탈선기,획득료량충가용적수체대분이분단지,유효지득도회수이용.
The synthesis of arbutin by use of thiolglycoside method was reported for the first time.Glucose was converted into a isopropyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside(donor) by acetylation,thiolation,deacetylation and benzoylation.Hydroquinone was selectively esterificated into two acceptors hydroquinone monoacetate,hydroquinone monobenzoate and related by-products(hydroquinone diesters).The donor was respectively coupled with two acceptors to afford two protected arbutins stereospecifically due to the effect of strong neighboring-group participation of C-2 benzoyl group,in which arbutin was obtained by use of deprotected methods respectively.All products were characterized by means of m.p.determination and 1HNMR analysis,etc.Additionally,two acceptors hydroquinone monoester could be obtained by effectively reusing the above by-products(diesters) via deacylating reaction.