480460-75-1

Basic information

• Product Name: 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate
• Synonyms: 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate
• CAS NO: 480460-75-1
• Molecular Weight: 349.384
• Mol File: 480460-75-1.mol

Chemical Properties

• CAS DataBase Reference: 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate(480460-75-1)
• EPA Substance Registry System: 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate(480460-75-1)

Safety Data

• Hazardous Substances Data: 480460-75-1(Hazardous Substances Data)

Upstream product

• 176436-12-7 2-benzyl 1-tert-butyl (2S)-6-oxo-1,2-piperidinedicarboxylate 
• 1027237-79-1 2-tert-butoxycarbonylamino-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-4-oxo-butyric acid benzyl ester 
• 480460-68-2 benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-(2,2-dimethyl-4,6-dioxo-1,3-dioxolan-5-yl)butanoate 
• 30925-18-9 2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 

Downstream Products

• 959937-52-1 3-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-2,2-dimethyl-N-(tetrahydropyran-4-yl)propionamide 
• 959937-91-8 N-{2-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-1,1-dimethylethyl}-2-(tetrahydropyran-4-yl)acetamide 
• 1005478-43-2 1-{2-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-1,1-dimethylethyl}-3-(tetrahydro-pyran-4-yl)urea 
• 1005478-44-3 4-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-3,3-dimethyl-1-(tetrahydropyran-4-ylamino)butan-2-one 
• 959937-93-0 {2-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-1,1-dimethyl-ethyl}carbamic acid benzyl ester 
• 959937-47-4 4-(3-methoxypropyl)-6-[(3R,6S)-1-(toluene-4-sulphonyl)-6-triisopropylsilanyloxy-methylpiperidin-3-yloxymethyl]-3,4-dihydro-2H-benzo[1,4]oxazine 
• 959937-48-5 4-(3-methoxypropyl)-6-[(3R,6S)-1-(toluene-4-sulphonyl)-6-triisopropylsilanyloxy-methylpiperidin-3-yloxymethyl]-4H-benzo[1,4]oxazin-3-one 
• 1005478-45-4 1-chloro-4-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-3,3-dimethylbutan-2-one 
• 959937-53-2 3-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-2,2-dimethyl-propionic acid 
• 959938-03-5 6-[(3R,6S)-6-(2-isocyanato-2-methylpropyl)-1-(toluene-4-sulphonyl)piperidin-3-yloxymethyl]-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine 
• 959937-54-3 methyl 3-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-2,2-dimethylpropionate 
• 959937-45-2 (2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-ylmethyl methanesulphonate 
• 959937-98-5 (R)-1-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-3-methylbutan-2-ol 
• 959937-92-9 2-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-2-yl]-1,1-dimethyl-ethylamine 

Relevant articles and documents

Diastereoselective hydroxylation of 6-substituted piperidin-2-ones. An efficient synthesis of (2S,5R)-5-hydroxylysine and related α-amino acids

The synthesis of (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylates (5) and related (3S,6R)-3-hydroxy-6-alkyl-2-oxo-1-piperidinecarboxylates has been developed. The approach is based on the asymmetric hydroxylation of enolates generated from the corresponding N-protected-6-substituted piperidin-2-ones. The utility of 5a as a precursor in the synthesis of (2S,5R)-5-hydroxylysine (1), an amino acid unique to collagen and collagen-like proteins, has also been demonstrated. (2S)-6-oxo-1,2-piperidinedicarboxylates (6) required for hydroxylation studies were prepared in 38-74% yield, starting from conveniently protected aspartic acid as inexpensive chiral adduct. Hydroxylation of 6 to 5 proceeds in high yield and excellent diastereoselectivity by treatment of their Li-enolate with (+)-camphorsulfonyloxaziridine at -78 °C. Ring opening of di-tert-butyl (2S,5R)-6-oxo-1,2-piperidinedicarboxylate ((5R)-5a) under reductive conditions afforded the corresponding 1,2-diol (17) in 91%, which was further transformed to (2S,5R)-5-hydroxylysine in four steps (84%). 17 is also a versatile intermediate in the preparation of tert-butyl (2S,5R)-2-[(tert-butoxycarbonyl)amino]-5-hydroxy-6-iodohexanoate (3) and tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-[(2R)-oxiranyl]-butanoate (4), two amino acid derivatives used in the total synthesis of the bone collagen cross-link (+)-pyridinoline (2a).