EurekaMag.com logo
+ Site Statistics
References:
52,725,316
Abstracts:
28,411,598
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Regioselective intramolecular ring closure of 2-amino-6-bromo-2,6-dideoxyhexono-1,4-lactones to 5- or 6-membered iminuronic acid analogues: synthesis of 1-deoxymannojirimycin and 2,5-dideoxy-2,5-imino-D-glucitol


Organic & Biomolecular Chemistry 6(10): 1779-1786
Regioselective intramolecular ring closure of 2-amino-6-bromo-2,6-dideoxyhexono-1,4-lactones to 5- or 6-membered iminuronic acid analogues: synthesis of 1-deoxymannojirimycin and 2,5-dideoxy-2,5-imino-D-glucitol
1-Deoxymannojirimycin (8c) was synthesised from 2-amino-6-bromo-2,6-dideoxy-D-mannono-1,4-lactone (7) by intramolecular direct displacement of the C-6 bromine employing non-aqueous base treatment followed by reduction of the intermediate methyl ester. Likewise, using aqueous base at pH 12, ring closure took place by 5-exo attack on the 5,6-epoxide leading to 2,5-dideoxy-2,5-imino-L-gulonic acid (9b), which was reduced to 2,5-dideoxy-2,5-imino-D-glucitol (9b). The method was further applied to 2-amino-6-bromo-2,6-dideoxy-D-galacto- as well as D-talo-1,4-lactones (14 and 15). However, only the corresponding six-membered ring 1,5-iminuronic acid mimetics, namely (2R,3R,4S,5R)-3,4,5-trihydroxypipecolic acid (2,6-dideoxy-2,6-imino-D-galactonic acid, 16) and (2S,3R,4S,5R)-3,4,5-trihydroxypipecolic acid (2,6-dideoxy-2,6-imino-D-talonic acid, 17), were obtained. The corresponding enantiomers, L-galacto- as well as L-talo-2-amino-6-bromo-2,6-dideoxy-1,4-lactones ent-14 and ent-15, reacted accordingly to give the D-galacto- and L-altro-1,5-iminuronic acid mimetics, (2S,3S,4R,5S)-3,4,5-trihydroxypipecolic acid (2,6-dideoxy-2,6-imino-L-galactonic acid, ent-16) and (2R,3S,4R,5S)-3,4,5-trihydroxypipecolic acids (2,6-dideoxy-2,6-imino-L-talonic acid, ent-17), respectively.


Accession: 055445703

PMID: 18452013

DOI: 10.1039/b719631h



Related references

Polyhydroxylated pyrrolidines from sugar lactones synthesis of 1 4 dideoxy 1 4 imino d glucitol from d galactonolactone and syntheses of 1 4 dideoxy 1 4 imino d allitol 1 4 dideoxy 1 4 imino d ribitol and 2s 3r 4s 3 4 dihydroxyproline from d gulonolactone. Tetrahedron 44(9): 2637-2648, 1988

Synthesis of deoxymannojirimycin fagomine deoxynojirimycin 2 acetamido 1 5 imino 1 2 5 trideoxy d mannitol 2 acetamido 1 5 imino 1 2 5 trideoxy d glucitol 2s 3r 4r 5r trihydroxypipecolic acid 2s 3r 4r 5s trihydroxypipecolic acid from methyl 3 o benzyl 2 6 dideoxy 2 6 imino alpha d mannofuranoside. Tetrahedron 43(5): 979-990, 1987

Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol. Organic Letters 14(16): 4174-4177, 2012

Synthesis of 1 5 dideoxy 1 5 imino d glucitol 1 deoxynojirimycin and 1 6 dideoxy 1 6 imino d glucitol from d glucofuranurono 6 3 lactone. Journal of Carbohydrate Chemistry 9(4): 479-500, 1990

Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol. Carbohydrate Research 435(): 100-105, 2016

Access to pyrrolidine imino sugars via tin(II)-mediated aldol reactions of bislactim ethers: synthesis of 2,5-dideoxy-2,5-imino-D-glucitol. Organic & Biomolecular Chemistry 6(21): 3967-3969, 2008

Total syntheses of (+)- and (-)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D- and L-glucitol) and of (+)- and (-)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-D- and L-iditol) via furoisoxazoline-3-aldehydes. Carbohydrate Research 314(1-2): 25-35, 1998

Amino acid mediated intramolecular asymmetric aldol reaction to construct a new chiral bicyclic enedione containing a seven-membered ring: remarkable inversion of enantioselectivity compared to the six-membered ring example. Journal of Organic Chemistry 72(1): 123-131, 2006

3 6 dideoxy 3 6 imino 1 2 o isopropylidene alpha d glucofuranose as a divergent intermediate for the synthesis of hydroxylated pyrrolidines synthesis of 1 4 dideoxy 1 4 imino l gulitol 1 4 dideoxy 1 4 imino d lyxitol 2s 3s 4r 3 4 dihydroxyproline and 1s 2r 8s 8ar 1 2 8 trihydroxyoctahydroindolizine 8 epi swainsonine x ray crystal structure of 1s 2r 8s 8ar 1 2 8 trihydroxy 5 oxooctahydroindolizine. Tetrahedron 43(13): 3095-3108, 1987

Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol. Organic Letters 4(5): 847-849, 2002