Trihydroxypipecolic acid

Trihydroxypipecolic acid (trihydroxylated piperidine) Uniflorine A (= 1,2,6,7,8-Pentahydroxyindolizidine) (indolizidine)... 

Fleet, G W J, Fellows, L E, Smith, P W, Synthesis of deoxymannojirimycin, fagomine, deoxynoj irimycin, 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol, 2-acetamido-1,5-imino-1,2, 5-trideoxy-D-glucitol, 25,3R,4R,5R-trihydroxypipecolic acid and 25,3R,4R,55-trihydrox3fpipecolic acid from methyl 3-0-benzyl-2,5-dideoxy-2,6-imino-a-D-mannofuranoside, Tetrahedron, 43, 979-990, 1987. 

Alternatively, an intramolecular nucleophilic displacement of a leaving group at C-2 by an amino group at C-6 has also been used for the synthesis of 1-deoxymannojirimycin (2) and (2S,31i ,41i ,51i )-3,4,5-trihydroxypipecolic acid (14) from diacetone D-glucose (4) (Scheme 2). Selective removal of the terminal isopropylidene group in 4 followed by selective tosylation of the primary hydroxyl group and subsequent Sn2 displacement of the... 

S,31, 47 ,55 )-3,4,5-Trihydroxypipecolic acid (1) was isolated from the seeds of legume Baphia racemosa Bak. It is a specific inhibitor of human fiver 3-D-glucuronidase and idouronidase but it has no effect on a- and p-glucosidases or mannosidases. (2S,4S,5S)-... 

Bacillus (1-deoxynojirimycin), 106 Bacillus (nojirimycin), 105 Baphia racemosa [(25,3, 4, 55)-3,4,5-trihydroxypipecolic acid)], 111... 

When the triflate (69 R=Bn) was treated with azide ion, inversion of configuration occurred to give a product which was converted to the /S-N-acetylglucosaminidase inhibitor (70), whilst (69 R=t-Bu) reacted with azide to give predominantly the product of retention of configuration, and thus ultimately (71).The aminoacid (2R, 3S, 4R)-dihydroxyproline (72) has been prepared from D-ribonolactone by a sequence which also Involved an unexpected replacement of triflate by azide with retention. The naturally occurring trihydroxypipecolic acid (73), its (2R)-... 

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