1-Amino-l-deoxy-D-glucitol

Panzer und Whistler (59) stellten aus Acrylsaure- bzw. Methacryl-saure anhydrid und 1-Amino-l-deoxy-D-glucitol (Glucamin) die ent-... 

Imidazole ring formation of acyclo C-nucleoside 543 was made by reaction of 6-chloro-l,3-dimethyl-5-nitrouracil with o-glucopyranosylamine (541), followed by catalytic hydrogenation and concomitant cyclization of 542 (67CB492). The same C-nucleoside (543) was obtained by reacting 1-amino-l-deoxy-D-glucitol (544) with 6-chloro-l,3-dimethyluracil and subsequent nitrosation and cyclization (96S459) (Scheme 145). 

Amino-l-deoxy-D-glucitol has been used as starting material for the preparation of 6-azido- and 6-amino-analogues or 7-caibonyl homologues (33, R = Me, Ph, NH2, OH) of 1-deoxynojirimycin. 

The chiral quaternary salt (12) of 1-amino-l-deoxy-D-glucitol,... 

Glucitol, 1-amino-l-deoxy-D-, 57 —, 2-amino-2-deoxy-n-, 57, 60 —, 1,4-anhydro-n-, 57 Glucofuranose, 1,2-0-isopropylidene-a-... 

Penta-O-Ac 2,3,4,5,6-Penta-O-acetyl-I-amino-l-deoxy-D-glucitol CisHzjNOio 391.374 Cryst. (EtOH aq.) (as hydrochloride). Mp 178-180° (hydrochloride). [a]o +1-5 (c, 0.7 in H2O) (hydrochloride). 

Freeman, F, Roharge, K D, Stereoselectivity in the electrophile-mediated cyclization of 2,3,5-tri-O-benzyl-L2-dideoxy-D-arafano-hex-l-enitol. A stereocontrolled s)mthesis of l-amino-2,5-anhydro-3, 4,6-tri-O-benzyl-l-deoxy-D-glucitol, Carbohydr. Res., 171, 1-H, 1987. 

Amino-N-octyl-l-deoxy-D-glucitol has been prepared from octyl-... 

Amino-6-deoxy-D-glucitol. 1-Amino-1 -deoxy-L-gulitol [134354-65-7]... 

Figure 1. Diagram illustrating the common nomenclature for polyhydroxylated piperidine alkaloids, (a) 5-Amino-5-deoxy-D-glucopyranose has the trivial name nojirimycin, (b) 1-deoxynojirimycin (DNJ) is the trivial name for l,5-dideoxy-l,5-imino-D-glucitol and similarly (c) 1-deoxymannojirimycin (DMJ) is the common name for l,5-dideoxy-l,5-imino-D-mannitol.

Full details of the synthesis of 6-azido-l,6-dideoxynojirimydn41 (see Vol 28, p. 227, ref. 52) from 1-amino-1-deoxy-D-glucitol via the intermediate azido sugar 40 have been reported together with its conversion to various analogues 42 of DNJ, and the bicyclic iminosugars castanospermine and kifunensine. ... 

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