158012-71-6

Upstream product

• 100-52-7 benzaldehyde 
• 40216-75-9 N-benzylidene-L-serine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123639-56-5 (S)-N-benzylserine methyl ester 

Downstream Products

• 209266-12-6 (S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 
• 158012-73-8 N-benzyl-N-tert-butoxycarbonyl-O-tert-butyldiphenylsilyl-L-serine methyl ester 
• 158012-72-7 methyl N-benzyl-O-((benzyloxy)methyl)-N-(tert-butoxycarbonyl)-L-serinate 
• 158012-78-3 N-benzyl-N-tert-butoxycarbonyl-O-tert-butyldiphenylsilyl-L-serinol 
• 158012-77-2 tert-butyl (R)-benzyl(1-((benzyloxy)methoxy)-3-hydroxypropan-2-yl)carbamate 
• 209266-19-3 Benzyl-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester 
• 209266-25-1 Benzyl-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements

To date, more than 100 congeners of the akuammiline alkaloid family have been isolated. Their signature structural element is a methanoquinolizidine moiety, a cage-like scaffold structurally related to adamantane. The structural variations of the family members originate from oxidative processes that mostly trigger rearrangements of the methanoquinolizidine motif. The family of the akuammiline alkaloids is best represented by strictamine. It bears the least functionalized carbon skeleton of all family members without lacking the signature structural motifs. Herein, we report the formal synthesis of strictamine through a Stevens [2,3]-sigmatropic rearrangement as a key step and the synthetic pitfalls related with its synthesis.

Substrate-Controlled Diastereoselectivity Reversal in NHC-Catalyzed Cross-Benzoin Reactions Using N-Boc-N-Bn-Protected α-Amino Aldehydes

The effectiveness of utilizing N-Bn-N-Boc-α-amino aldehydes in cross-benzoin reactions with heteroaromatic aldehydes is demonstrated. The reaction is both chemoselective and syn-selective, making it complementary to the anti-selective cross-benzoin reaction of NHBoc-α-amino aldehydes. Good diastereoselectivity is obtained for a variety of amino aldehydes, including nonhindered ones. A Felkin-Anh model can be used to rationalize the observed diastereoselectivity.

A versatile synthesis of (+)-deoxoprosopinine and (-)-deoxoprosophylline

An efficient synthesis of (+)-deoxoprosopinine and (-)-deoxoprosophylline was achieved from N-benzyl-N-Boc serine derivatives (7) and (7′).

Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation

The TEMPO oxidation method is successfully applied to preparation of variously protected, optically active α-amino aldehydes without racemization and in very good yield.

Synthesis of N,N-Diprotected L-Serinals

Four variously protected L-serinals have been synthesized from L-serine via reduction of the respective methyl esters followed by the Swern oxidation.Key words: Serinals, protecting groups, amino aldehydes, synthesis