Studies on reactivity of azidoamides, intermediates in the synthesis of tetrahydroxypipecolic acid derivatives

Azido group reduction was observed by the treatment of a 2-azido-3-triisopropylsilyloxy heptonamide derivative with NaI in DMSO. The process allowed us to obtain a tetrahydroxypipecolic acid amide derivative. The same azido amide was treated with LiCl in DMSO, but desilylation occurred to give 3,6-anhydro-2-azido heptonamide.

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2-Azido-N,N-diethyl-4,5-O-isopropylidene-7-O-trityl-d-glycero-d-allo-heptonamideC33H40N4O6[α]D21=-28 (c 1.1, CHCl3)Source of chirality: d-ribose and stereoselective syntheses

2-Azido-N,N-diethyl-4,5-O-isopropylidene-3-O-triisopropylsilil-7-O-trityl-d-glycero-d-allo-heptonamideC42H60N4O6Si[α]D22=-10 (c 0.3, CH2Cl2)Source of chirality: d-ribose and stereoselective syntheses

2-Azido-N,N-diethyl-4,5-O-isopropylidene-6-O-mesyl-3-O-triisopropylsilil-7-O-trityl-d-glycero-d-allo-heptonamideC43H62N4O8SSi[α]D20=+24 (c 0.37, CH2Cl2)Source of chirality: d-ribose and stereoselective syntheses

N,N-Diethyl-2,6-dideoxy-2,6-imino-4,5-O-isopropylidene-7-O-trityl-l-glycero-d-allo-heptonamideC42H60N2O5Si[α]D22=-10.5 (c 0.26, CH2Cl2)Source of chirality: d-ribose, stereoselective syntheses and stereospecific cyclization

3,6-Anhydro-2-azido-N,N-diethyl-4,5-O-isopropiliden-7-O-trityl-l-glicero-d-allo-heptonamideC33H38N4O5[α]D25=+7.5 (c 1.5, CHCl3)Source of chirality: d-ribose, stereoselective syntheses and stereospecific cyclization

2,3-Anhydro-N,N-diethyl-4,5-O-isopropylidene-6-O-mesyl-7-O-trityl-d-glycero-d-altro-heptonamideC34H41NO8S[α]D20=-6 (c 1.01, CH2Cl2)Source of chirality: d-ribose and stereoselective synthesis