117183-90-1

Basic information

• Product Name: (1S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-1-[(S)-(4-methoxy-benzyloxy)-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione
• Synonyms: (1S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-1-[(S)-(4-methoxy-benzyloxy)-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione
• CAS NO: 117183-90-1
• Molecular Weight: 696.913
• Mol File: 117183-90-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-1-[(S)-(4-methoxy-benzyloxy)-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-1-[(S)-(4-methoxy-benzyloxy)-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione(117183-90-1)
• EPA Substance Registry System: (1S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-1-[(S)-(4-methoxy-benzyloxy)-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione(117183-90-1)

Safety Data

• Hazardous Substances Data: 117183-90-1(Hazardous Substances Data)

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 95237-57-3 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 117249-39-5 (1S,6R)-6-(tert-butyldimethylsilyl)-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 95237-55-1 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-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 
• 95237-56-2 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 79243-92-8 (S)-(-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde 

Downstream Products

• 38129-37-2 Aizumycin 
• 117183-92-3 (1S,6R)-6-hydroxy-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7-(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 117183-91-2 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7-(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 

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.