N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Base Information

Chemical Name:N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester
CAS No.:742102-97-2
Molecular Formula:C₂₅H₃₈N₂O₇S
Molecular Weight:510.652
Hs Code.:

Synonyms:N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

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Chemical Property of N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

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Technology Process of N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

There total 9 articles about N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

: 2491-18-1
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

: 742102-83-6
(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

: 742102-97-2
N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
DOI:10.1021/jm049927q

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 742102-97-2
N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂

2: 0.60 g / NaOMe / methanol

3: 77 percent / (+)-camphorsulfonic acid / acetonitrile / 65 °C

4: DIBAL-H / toluene / 0 °C

5: 100 percent / aq. KOH; K₂S₂O₈; RuCl₃*3H₂O / acetonitrile

6: 83 percent / HOBt; BOP; DiPEA / dimethylformamide

With ruthenium trichloride; potassium hydroxide; dipotassium peroxodisulfate; sodium methylate; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: 229473-28-3
2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose

: 742102-97-2
N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / (+)-camphorsulfonic acid / acetonitrile / 65 °C

2: DIBAL-H / toluene / 0 °C

3: 100 percent / aq. KOH; K₂S₂O₈; RuCl₃*3H₂O / acetonitrile

4: 83 percent / HOBt; BOP; DiPEA / dimethylformamide

With ruthenium trichloride; potassium hydroxide; dipotassium peroxodisulfate; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q