✍ Scribed by Albert Defoin; Hervé Sarazin; Jacques Streith
No coin nor oath required. For personal study only.
Nucleophilic ring opening of the cyclic sulfates (+)-9c and D-9c and of the epoxide (+)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder aAhwt of h~ldicnal dime~ylac~tai to aehiral or enantiometieally pure nitroso-derivatives) led to ~xynojirimycin and 6-deoxy-gu/o..nojirimycin in the raeemic and D-series, to ~fuco-nojirimyein and to tl~ir l-deoxydexivatives v/a their crystalline 1-deoxy-l-sulfonie acid derivatives (suUim adduets). 6-Dcoxy-nojirimycin and its isomers are mixtures of a-and 13-anomers and of the conv, s~nding imine.
📜 SIMILAR VOLUMES
## Abstract Asymmetric __Diels‐Alder__ reaction of sorbaldehyde __O__‐methyloxime 1d with chiral chloronitroso derivative 2 of D‐mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; __Scheme 1__). Catalytic hydrogenolysis of 6a gave