857894-35-0

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 141943-06-8 1,7-heptanediol monobenzyl ether 
• 129649-05-4 7-benzyloxyheptan-1-ol 
• 857894-33-8 (R_SR,R)-(-)-methyl 3-oxo-5-(6-benzyloxyhexyl)-5-(p-toluenesulfinylamino)pentanoate 
• 857894-32-7 (R_SR,R)-(-)-methyl 3-(6-benzyloxyhexyl)-3-(p-toluenesulfinylamino)propanoate 
• 857894-31-6 (R)-(-)-7-benzyloxyheptylidene-p-toluenesulfonimide 
• 857894-34-9 (R)-(-)-6-(6-benzyloxyhexyl)-4-oxo-5,6-dihydro-4H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 

Downstream Products

• 857894-36-1 (R)-(+)-6-(6-benzyloxyhexyl)-4-(tert-butyldimethylsilanyloxy)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 
• 303007-77-4 (3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 1026863-60-4 6-[6-(tert-butyl-diphenyl-silanyloxy)-hexyl]-4-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 

Relevant academic research and scientific papers

Unique divergent reactivity of Boc-protected homopropargylic alkoxyalkylamines in the gold(I)-catalyzed domino catalytic reactions: Application to the formal synthesis of (-)-pseudodistomin B

By using t-Boc-protected homopropargylic alkoxyalkylamines as substrates, the reactivity between the carboxylation-promoted and the alkoxylation-promoted domino processes in the gold-catalyzed reaction was systematically compared. Interestingly, the resul

Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfinimine-derived δ-amino β-ketoesters. Formal synthesis of pseudodistomin B triacetate

N-Sulfinyl δ-amino β-ketoester enaminones, a new sulfinimine-derived chiral building block, undergoes, on hydrolysis in one pot, an intramolecular Michael addition followed by a retro-Michael-type elimination to give enantiopure 2,4,5-trisubstituted piper

General Route to 2,4,5-Trisubstituted Piperidines from Enantiopure ss-Amino Esters. Total Synthesis of Pseudodistomin B Triacetate and Pseudodistomin F

The Michael addition reaction of enantiopure ss-amino esters with methyl acrylate followed by Dieckmann condensation and enol silylation affords the enol ethers 6, which are hydrogenated with catalysis by Raney-Ni at 80 atm and 80°C to provide 2,4,5-trisubstituted piperidines with high diastereoselectivity. In this case Ni-H attacks the C-C double bond from the direction of the 2-alkyl group to provide the products in which 2,4,5-trisubstrited groups are all cis to each other. While hydrogenation of enol ether 13 without a N-Boc protecting group gives the product 15 in which the 4-hydroxy group and 5-ester moiety are trans to the 2-alkyl group. By using the diastereoselective hydrogenation products 9d and 9e as key intermediates, pseudodistomin B triacetate and pseudodistomin F are synthesized. The key steps for these transformations include Curtius rearrangement and Julia olefination.