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药物详细合成路线

Name Miglitol;SK-983;Bay-m-1099;Plumarol;Diastabol;Glyset
Chemical Name 1,5-Dideoxy-1,5-[(2-hydroxyethyl)imino]-D-glucitol
      (2R,3R,4R,5S)-1-(2-Hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidinetriol
CAS 72432-03-2
Related CAS
Formula C8H17NO5
Structure
Formula Weight 207.22839
Stage 上市-1998
Company Bayer (Originator), Lacer (Licensee), Pfizer (Licensee), Sanofi-synthélabo (Licensee), Sanwa (Licensee)
Activity/Mechanism Antidiabetic Drugs, ENDOCRINE DRUGS, Type 2 Diabetes Mellitus, Agents for, alpha-Glucosidase Inhibitors, Iminosugars
Syn. Route 1
Route 1
a new synthesis of miglitol has been reported:reaction of the bromoglycoside (i) with ethanolamine (ii) by means of zn and nabh3cn in refluxing propanol/water gives the adduct (iii), which is benzylated with benzyl chloride and nah in dmf yielding compound (iv). the cyclization of (iv) by means of mercury trifluoroacetate in thf, followed by a treatment with khco3 and kbr affords a mixture of the diastereomeric organomercuric piperidines (v) and (vi) which are separated by chromatography. the desired diastereomer (vi) was treated with o2 and nabh4 in dmf to give the protected piperidinemethanol (vii), which is finally debenzylated by hydrogenolysis with h2 over pd/c in ethanol. the undesired diastereomer (v) can be recovered by swern oxidation giving aldehyde (viii), isomerization of (viii) with dbu to provide aldehyde (ix) and reduction of (ix) to the already reported piperidinemethanol (vii).
List of intermediates No.
(1s,2s,3r,4s,7r,9s,10s,12r,15s)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate (ii)
2-bromo-5-(1,3-oxazol-2-yl)benzaldehyde (i)
n-(4,5-dimethyl-3-isoxazolyl)-2-formyl-n-[(2-methoxyethoxy)methyl]-4-(1,3-oxazol-2-yl)[1,1-biphenyl]-2-sulfonamide (iii)
n-(4,5-dimethyl-3-isoxazolyl)-2-formyl-4-(1,3-oxazol-2-yl)[1,1-biphenyl]-2-sulfonamide (iv)
n-(4,5-dimethyl-3-isoxazolyl)-n-methyl-2-[(methylamino)methyl]-4-(1,3-oxazol-2-yl)[1,1-biphenyl]-2-sulfonamide (v)
2-{2-[(2-aminoethyl)amino]ethyl}-5-nitro-1h-benzo[de]isoquinoline-1,3(2h)-dione (vi)
3-(tert-butyl)-1-(4-methylphenyl)-1h-pyrazol-5-amine; 3-(tert-butyl)-1-(4-methylphenyl)-1h-pyrazol-5-ylamine (vii)
2,2,2-trichloroethyl 3-(tert-butyl)-1-(4-methylphenyl)-1h-pyrazol-5-ylcarbamate (viii)
4-[2-(4-morpholinyl)ethoxy]-1-naphthalenamine; 4-[2-(4-morpholinyl)ethoxy]-1-naphthylamine (ix)
Reference 1:
    therisod, m.; fouacea, s.; lipophilic prodrugs of 1-deoxynojirimycin derivatives. tetrahedron lett 2000, 41, 38, 7313.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名米格列醇;英文名Miglitol;SK-983;Bay-m-1099;Plumarol;Diastabol;Glyset;CAS[72432-03-2]

 
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