114886-54-3

Basic information

• Product Name: Carbamic acid, [5-[[(1,1-dimethylethoxy)carbonyl]amino]-6-[(methylsulfonyl)oxy]hexyl]-, phenylmethyl ester, (S)-
• CAS NO: 114886-54-3
• Molecular Formula: C20H32N2O7S
• Molecular Weight: 444.549
• Mol File: 114886-54-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [5-[[(1,1-dimethylethoxy)carbonyl]amino]-6-[(methylsulfonyl)oxy]hexyl]-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [5-[[(1,1-dimethylethoxy)carbonyl]amino]-6-[(methylsulfonyl)oxy]hexyl]-, phenylmethyl ester, (S)-(114886-54-3)
• EPA Substance Registry System: Carbamic acid, [5-[[(1,1-dimethylethoxy)carbonyl]amino]-6-[(methylsulfonyl)oxy]hexyl]-, phenylmethyl ester, (S)-(114886-54-3)

Safety Data

• Hazardous Substances Data: 114886-54-3(Hazardous Substances Data)

Upstream product

• 84890-96-0 C₂₄H₃₆N₂O₈ 
• 2389-45-9 Boc-Lys(Z)-OH 
• 82689-20-1 N⁶-benzyloxycarbonyl-N²-tert-butoxycarbonyl-L-lysinol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 190904-32-6 (S)-benzyl tert-butyl (6-cyanohexane-1,5-diyl)dicarbamate 
• 153074-77-2 (S)-3-Amino-7-benzyloxycarbonylamino-heptanoic acid methyl ester 

Relevant articles and documents

Synthesis of a series of ω-dimethylaminoalkyl substituted ethylenediamine ligands for use in enantioselective catalysis

The title compounds H2NCH((CH2)nNMe2)CH2NH2 L1-L4 (n = 1-4) are efficiently synthesized in enantiopure form. The commercial starting materials, l-asparagine, (S)-5-hydroxymethyl-2-pyrrolidinone, and (S)-6-(((benzyloxy)carbonyl)-amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid, are elaborated in 6-9 standard steps to give L1 (18% overall), L2 (13%), L3 (36%) and L4 (38%) or the corresponding tris(hydrochloric acid) salts [H3NCH((CH2)nNHMe2)CH2NH3]3+ 3Cl-, which are preferable for long term storage. The sequences make use of isobutyl carbamate, Cbz, and Boc protecting groups and Hofmann type rearrangements; the dimethylamino groups are introduced at late stages, either via reductive dimethylations or nucleophilic displacements involving mesylates and HNMe2. L1-L4 chelate to [Co(en)2]3+ fragments to give octahedral complexes that catalyze numerous enantioselective reactions.

Synthesis of chiral triamines and diamines from amino acids

Selectively protected (2S)-1,2,6-triaminohexane 4 was prepared from L-lysine by reduction of the amino acid, replacement of the hydroxy group by an azido group and selective reduction. Following the same method vicinal diamines 11 and 13 bearing a third functional group were synthesized from L-glutamic acid.