92098-16-3

Basic information

• Product Name: 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione
• Synonyms: 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione
• CAS NO: 92098-16-3
• Molecular Weight: 438.48
• Mol File: 92098-16-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione(92098-16-3)
• EPA Substance Registry System: 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione(92098-16-3)

Safety Data

• Hazardous Substances Data: 92098-16-3(Hazardous Substances Data)

Upstream product

• 117249-35-1 (1S,6R)-6-hydroxy-7,9-bis(p-methoxybenzyl)-7,9-diaza-2-oxabicyclo<4.2.2>decane-5,8,10-trione 
• 117249-34-0 (1S,6R)-5,6-dihydroxy-7,9-bis(p-methoxybenzyl)-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 94807-48-4 4-(2-Benzyloxy-ethyl)-6,9-bis-(4-methoxy-benzyl)-2,2-dimethyl-1,3-dioxa-6,9-diaza-spiro[4.5]decane-7,10-dione 
• 94807-50-8 (1S,9R)-10,12-Bis-(4-methoxy-benzyl)-3,3-dimethyl-2,4,8-trioxa-10,12-diaza-tricyclo[7.2.2.0^1,5]tridecane-11,13-dione 
• 94807-49-5 4-(2-Hydroxy-ethyl)-6,9-bis-(4-methoxy-benzyl)-2,2-dimethyl-1,3-dioxa-6,9-diaza-spiro[4.5]decane-7,10-dione 
• 94807-52-0 6-hydroxy-7,9-bis(p-methoxybenzyl)-2-oxa-7,9-diazabicyclo<4.2.2>decane-5,8,10-trione 
• 94807-46-2 9-Acetyl-4-(2-benzyloxy-ethyl)-2,2-dimethyl-1,3-dioxa-6,9-diaza-spiro[4.5]decane-7,10-dione 
• 94807-45-1 1-Acetyl-3-(3-benzyloxy-1-hydroxy-propyl)-3-hydroxy-piperazine-2,5-dione 
• 94807-47-3 4-(2-Benzyloxy-ethyl)-2,2-dimethyl-1,3-dioxa-6,9-diaza-spiro[4.5]decane-7,10-dione 
• 92216-27-8 1,4-dimethyl-3-(2'-thiopyridyl)-6-(2-γ-butyrolactonyl)-2,5-piperazinedione (anti, major diastereomer) 
• 92098-11-8 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-(2-γ-butyrolactonyl)-2,5-piperazinedione (syn, major diastereomer) 
• 92216-26-7 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-(2-γ-butyrolactonyl)-2,5-piperazinedione (syn, minor diastereomer) 
• 92098-03-8 syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer) 
• 92216-29-0 anti-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer) 

Downstream Products

• 92125-62-7 N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin 
• 95694-73-8 (+)-N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin 
• 38129-37-2 Aizumycin 
• 38129-37-2 (+/-)-bicyclomycin 
• 95694-70-5 (1S,6R)-6-hydroxy-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 94807-54-2 6-(t-butyldimethylsilyloxy)-1,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo<4.2.2>decane-8,10-dione 
• 92098-17-4 N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin 

Relevant articles and documents

Chiral Synthesis of Bicyclomycin and Diastereomeric Stereoselectivity of the Key Aldol Condensation

Optically pure bicyclomycin (1) was synthesized via aldol condensation of racemic 7,9-bis(p-methoxybenzyl)-5-methylene-6--7,9-diaza-2-oxabicyclodecane-8,10-dione (2) with 2,3-di-O-isopropylidene-2-C-methyl-L-glyceraldehyde (3).The major condensation product 4 was then N-de(p-methoxybenzyl)ated and O-deisopropylidenated simultaneously with CAN and O-de(tert-butyldimethylsilyl)ated with Bu4NF under finely optimized conditions, respectively, to give 1.The structures of three other diastereomers of 4 were elucidated through comparisonwith the products of the aldol condensation of optically pure 2 and 3.The compounds (+)-2 and (-)-2 were prepared by diastereomeric separation of the synthetic precursor of 2, i.e., 5,6-dihydroxy-7,9-bis(p-methoxybenzyl)-7,9-diaza-2-oxabicyclodecane-8,10-dione as its (-)-MTPA ester, followed by the previously established four-step conversion.The stereoselectivity of the aldol condensation was explained by the chair conformation-like transition states.

Stereocontrolled Total Synthesis of (+/-)- and (+)-Bicyclomycin

The completely regio- and stereocontrolled total synthesis of bicyclomycin (1) is described in 12 chemical steps.A new carbon-carbon bond-forming reaction on 1,4-dibenzyl- and 1,4-bis(p-methoxybenzyl)-3,6-bis(2'-thiopyridyl)-2,5-piperazinediones (10 and 4

Stereocontrolled total synthesis of (±)- and (+)-bicyclomycin: New carbon-carbon bond-forming reactions on electrophilic glycine anhydride derivatives

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