208647-77-2

Upstream product

• 1254054-91-5 C₁₈H₂₇NO₆ 
• 5437-45-6 Benzyl bromoacetate 
• 108466-89-3 N-(tert-butyloxycarbonyl)-8-amino-3,6-dioxaoctanoic acid 

Downstream Products

• 1254054-66-4 C₁₉H₂₈N₄O₇ 

Relevant academic research and scientific papers

Method for synthesizing semaglutide side chain in liquid-phase convergent manner

The invention discloses a method for synthesizing a semaglutide side chain 1 in a liquid-phase convergent manner. The method comprises the steps: protecting amino of a raw material 2-(2-aminoethoxy)ethanol by using R1; then carrying out nucleophilic substitution reaction with ethyl bromoacetate; carrying out ester hydrolysis in one pot to obtain a compound 4; protecting carboxyl of the compound 4with R2; removing R1 to obtain a compound 6; carrying out condensation reaction on the compound 6 and fluorenylmethoxycarbonyl-L-glutamic acid 1-tert-butyl ester, to obtain a compound 8; removing R2 of the compound 8, and carrying out a coupling reaction with the compound 6 to obtain a compound 10; removing Fmoc of the compound 10, carrying out an amidation condensation coupling reaction with 18-(tert-butoxy)-18-oxooctadecanoic acid to obtain a compound 13; and removing R2 of the compound 13 to obtain the product 1. The method has the advantages of effective and controllable synthesis process,low cost and high yield, and can be suitable for large-scale production.

Convergent liquid-phase synthesis method of semaglutide side chain

A synthesis method of a semaglutide side chain 1 comprises the following steps: protecting a terminal amino group of a raw material diglycolamine 2 by using R1, then carrying out nucleophilic substitution reaction with alpha halogenated ester, and carrying out ester hydrolysis in one pot to obtain a compound 4; protecting the free carboxyl of the compound 4 by R2, and removing the R1 protected group to obtain a compound 6; carrying out condensation reaction on a compound 7 and the compound 6 to obtain a compound 8; removing fluorenylmethoxycarbonyl of the compound 8, carrying out an amidationcondensation coupling reaction on the compound 8 and 18-(tert-butoxy)-18-oxooctadecanoic acid to obtain a compound 11; removing the R2 protected group of the compound 11, carrying out a condensation coupling reaction on the compound 11 and the compound 6 to obtain a compound 13; and removing the R2 protected group of the compound 13 to obtain the chain 1. A convergent synthesis method is used to reduce the reaction cost and shorten the reaction time, the synthesis process is effective and controllable, the cost is low, the yield is high, and the method is suitable for large-scale production.

Method for preparing semaglutide side chain by liquid phase method

The invention discloses a method for preparing a semaglutide side chain. The preparation method comprises the following steps: protecting amino of an initial raw material 2-(2-aminoethoxy) ethanol byusing R1; then carrying out nucleophilic substitution reaction with alpha halogenated ester to prolong a carbon chain; preparing an aliphatic chain with two protected ends by a one-pot method; removing a protecting group at one end of each aliphatic chain and condensing to obtain a compound 7; removing the R1 protecting group to obtain a compound 8, performing condensation reaction on the compound8 and fluorenylmethoxycarbonyl-L-glutamic acid 1-tert-butyl ester to obtain a compound 10, removing the fluorenylmethoxycarbonyl, performing amidation condensation reaction on the compound 10 and 18-(tert-butoxy)-18-oxooctadecanoic acid to obtain a compound 13, and removing the R2 protecting group to obtain a target product chain 1. Compared with solid-phase synthesis, the method disclosed by theinvention is lower in cost and wider in selection of protecting groups, and has industrial production and application prospects.

Liquid-phase synthesis method of semaglutide side chain

The invention discloses a liquid-phase synthesis method of a semaglutide side chain. The liquid-phase synthesis method comprises the following steps: taking diglycolamine and an X radical to react, soas to protect an amino terminal of the diglycolamine through the X radical; then realizing hydroxyl protection through the amino terminal and a reaction carboxyl terminal of benzyl bromoacetate, so as to remove benzyl and the X radical; after coupling two products without the radical, removing the X radical; then coupling with an Fmoc-glutamic acid and removing Fmoc; finally coupling with 18-(tert-butoxy)-18oxooctadecanoic acid and then removing the benzyl to obtain the semaglutide side chain. The method disclosed by the invention has the advantages that a synthesis method process is feasible, controllable, low in cost and high in yield; the synthesis method is applicable to large-scale production; the semaglutide side chain is finally prepared and can be directly assembled to a semaglutide main chain in a liquid phase after being modified into OSu ester.

A universal and ready-to-use heterotrifunctional cross-linking reagent for facile synthetic access to sophisticated bioconjugates

We describe for the first time, the synthesis and some bioconjugation applications of an original heterotrifunctional cross-linking reagent (also named tripod) bearing three different bioorthogonal functional groups which are fully compatible amongst themselves. Contrary to the first generation tripod recently reported by us (Org. Biomol. Chem., 2008, 6, 3065), the use of an azido group instead of the nucleophile-sensitive active carbamate moiety enables us to reach the targeted chemical orthogonality without the use of temporary aminooxy- and thiol protecting groups. Thus, the preparation of sophisticated bioconjugates through the sequential derivatisation of the tripod by means of copper-mediated 1,3-dipolar cycloaddition, oxime ligation and aqueous compatible mild thiol-alkylation reactions, is significantly simpler and more convenient. The chemoselective bioconjugation protocols were optimised through the preparation of FRET cassettes based on cyanine and/or xanthene fluorescent dye pairs and subsequent anchoring to fragile biomolecules. The applicability of this universal cross-linking reagent was also illustrated by the preparation of biochips suitable for aflatoxin B1 detection through the SPIT-FRI method.