181705-71-5

Basic information

• Product Name: (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one
• Synonyms: (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one
• CAS NO: 181705-71-5
• Molecular Weight: 423.627
• Mol File: 181705-71-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one(181705-71-5)
• EPA Substance Registry System: (5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one(181705-71-5)

Safety Data

• Hazardous Substances Data: 181705-71-5(Hazardous Substances Data)

Upstream product

• 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 
• 81658-25-5 2-hydroxymethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 181705-70-4 (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone 
• 181705-84-0 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 267661-32-5 Acetic acid (3S,6R,8aS)-6-benzyl-3-formyl-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-31-4 Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-35-8 Acetic acid (3S,6S,8S,8aS)-6-benzyl-3-formyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-14-3 (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid 
• 267661-15-4 Acetic acid (3S,6S,8S,8aS)-6-benzyl-3-hydroxymethyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-36-9 (3S,6S,8S,8aS)-6-Acetoxy-6-benzyl-8-methoxy-5-oxo-octahydro-indolizine-3-carboxylic acid 
• 743423-44-1 (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-methoxyhexahydroindolizin-5-one 
• 267661-41-6 (3S,6S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-6-methyl-hexahydro-indolizin-5-one 
• 267661-40-5 (3S,6S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-6-methyl-hexahydro-indolizin-5-one 
• 267661-42-7 Acetic acid (3S,6S,8aS)-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-oxo-octahydro-indolizin-6-yl ester 
• 267661-30-3 (3S,6R,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one 
• 267661-10-9 (3S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-8-(4-methoxy-benzyloxy)-hexahydro-indolizin-5-one 
• 267661-29-0 (3S,6S,8S,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-6,8-dihydroxy-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 

Relevant articles and documents

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.

A versatile synthesis of a β-turn peptidomimetic scaffold: An approach towards a designed model antagonist of the tachykinin NK-2 receptor

A general and stereocontrolled synthesis of an azabicyclo[4.3.0]nonane amino acid template with an appended substitutent at C-5 was developed. The approach allows for stereochemical and functional variations that extend the utility of these rigid amino acid motifs as peptidomimetics. The synthesis of a weakly active but specific NK-2 receptor antagonist is described.