Carotinoid‐Glycosylester. 3. Mitteilung. Die synthese von crocetin‐di‐(β‐D‐glucosyl)‐ester. Eine neue methode zur selektiven veresterung von ungeschützter β‐D‐glucose

Abstract

The naturally occurring crocetin-di-(P-D-glucosyl) ester is easily synthesized by the reaction of crocetin-di-imidazolide or crocetin-di-( 1,2,4.-triazolide) and unprotected P-D-glucose in pyridine in presence of a base (Scheme 4). Under the described experimental conditions the esterification takes place exclusively at the anomeric C-atom and furthermore produces only the p-anomer. It is the first time that an unprotected carbohydrate has been used for the selective synthesis of glucosyl esters at the anomeric C-atom. This represents the major advantage of this new method.

A Short and Efficient Synthesis of Crocetin-dimethylester and Crocetindial

“…Crocin ( 3 ) and crocetin ( 4 ) esters are the coloring principles of saffron, which find uses in medicine as well as flavoring and coloring agents . The crocetin-dimethylester ( 1 ) is a very useful compound because it can be easily converted to crocetindial ( 2 ) and crocin or crocetin derivatives, and can be used as starting material for the syntheses of carotenoids and many other natural products. ,4a, …”

Straightforward Synthesis of 2-Acetamido-2-deoxy-β-d-glucopyranosyl Esters under Microwave Conditions

“…6 Acyl glucuronides are metabolite products of myco-phenolic acid 7 and nonsteroidal anti-inflammatory drugs such as ibuprofen, naproxen, and diclofenac. 8 Synthesis of glycosyl esters has been achieved using coupling reagents such as DCC, 9 imidazole, 10 by Mitsunobu reaction, 3,11 Yamaguchi anhydride derivative, 12 or with assistance of a C-2 participating neighboring group. 13 A glycosyl trichloroacetimidate has been used to synthesize ester-linked glycosyl dopamine derivatives as potential antiparkinsonian prodrugs.…”