181705-84-0

Upstream product

• 181705-70-4 (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 
• 81658-25-5 2-hydroxymethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 782496-03-1 (2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine 
• 192389-43-8 (5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine 
• 185303-86-0 N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-L-arabinoheptono-1,4-lactam 
• 141393-87-5 4-<(tert-butoxycarbonyl)amino>-6,7-O-isopropylidene-2,3,4-trideoxy-L-arabino-hept-2-enonic acid 1,4-lactam 
• 185303-87-1 tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 

Downstream Products

• 244274-69-9 (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one 
• 244274-73-5 8-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-indolizine 
• 267661-37-0 Acetic acid (3S,6S,8S,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-12-1 (3S,6S,8S,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-8-(4-methoxy-benzyloxy)-hexahydro-indolizin-5-one 
• 267661-33-6 Acetic acid (3S,6R,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-38-1 [1-Amino-1-(4-{[((3S,6S,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester 
• 267661-34-7 [1-Amino-1-(4-{[((3S,6R,8aS)-6-benzyl-6-hydroxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester 
• 267661-11-0 (3S,6S,8S,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-8-(4-methoxy-benzyloxy)-hexahydro-indolizin-5-one 
• 267661-17-6 (3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-8-(4-methoxy-benzyloxy)-6-methyl-hexahydro-indolizin-5-one 
• 267661-13-2 Acetic acid (3S,6R,8aS)-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-39-2 (3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-8-(4-methoxy-benzyloxy)-6-methyl-hexahydro-indolizin-5-one 
• 267661-45-0 [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester 
• 267661-29-0 (3S,6S,8S,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-hexahydro-indolizin-5-one 
• 267661-10-9 (3S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-8-(4-methoxy-benzyloxy)-hexahydro-indolizin-5-one 

Relevant academic research and scientific papers

Exploring the chiral space within the active site of α-thrombin with a constrained mimic of D-Phe-Pro-Arg - Design, synthesis, inhibitory activity, and X-ray structure of an enzyme-inhibitor complex

An indolizidinone motif with strategically placed substitutents was designed and synthesized as a constrained mimic of D-Phe-Pho-Arg. Low nanomolar inhibition of α-thrombin validates the design elements in this inhibitor which also exhibits a 20-fold selectivity for thrombin versus trypsin. An X-ray crystal structure of the inhibitor with α-thrombin shows the expected interactions with key amino acids within the active site and some notable changes in positions. (C) Elsevier Science Ltd. All rights reserved.

Lewis acid assisted vinylogous Mannich and Mukaiyama aldol reactions: A route to densely hydroxylated indolizidine alkaloid analogues

The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine-australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)- glyceraldehyde 9.