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Category Enzyme inhibitors
Catalog number BBF-01826
CAS 84444-90-6
Molecular Weight 163.17
Molecular Formula C6H13NO4

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It is produced by the strain of Streptomyces lavendulae. Deoxymannojirimycin is a powerful enzyme inhibitor.


IUPAC Name (2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol
Canonical SMILES C1C(C(C(C(N1)CO)O)O)O
InChI InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4-,5-,6-/m1/s1


Melting Point 188°C

Reference Reading

1. Asymmetric Syntheses of (-)-ADMJ and (+)-ADANJ: 2-Deoxy-2-amino Analogues of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin
Stephen G Davies, Aude L A Figuccia, Ai M Fletcher Paul, M Roberts, James E Thomson J Org Chem. 2016 Aug 5;81(15):6481-95. doi: 10.1021/acs.joc.6b01107. Epub 2016 Jul 15.
The asymmetric syntheses of (-)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-opening of the corresponding aziridinium intermediates with a tethered carbamate moiety) to give oxazolidin-2-ones was initially optimized on a model system. Subsequent application of this methodology to two enantiopure bishomoallylic amines (which were produced via aminohydroxylation of an α,β-unsaturated ester, partial reduction, and reaction of the corresponding aldehyde with vinylmagnesium bromide) also proceeded with concomitant N-debenzylation to afford the corresponding diastereoisomerically pure (>99:1 dr) oxazolidin-2-ones. Subsequent deprotection of these enantiopure templates gave (-)-ADMJ and (+)-ADANJ as single diastereoisomers in 16% and 24% overall yield, respectively.
2. Synthesis of 1-Deoxymannojirimycin from d-Fructose using the Mitsunobu Reaction
Peter Sunde-Brown, Ian D Jenkins, Todd A Houston J Org Chem. 2022 Dec 16;87(24):16895-16901. doi: 10.1021/acs.joc.2c02174. Epub 2022 Dec 2.
Three different Mitsunobu reactions have been investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ) from d-fructose. The highest yielding and most practical synthesis can be undertaken on a 10 g scale with minimal chromatography. In the key step, N,O-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-α-d-fructofuranose under Mitsunobu conditions to give 14. Acidic hydrolysis affords nitrone 15, which reduces quantitatively via catalytic hydrogenolysis to afford 1-DMJ (4) in 55% overall yield from d-fructose (cf. 37% for azide route and 29% for nosyl route).
3. Asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin via a ring-expansion approach
Stephen G Davies, Aude L A Figuccia, Ai M Fletcher, Paul M Roberts, James E Thomson Org Lett. 2013 Apr 19;15(8):2042-5. doi: 10.1021/ol400735z. Epub 2013 Apr 9.
The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40

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