N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Base Information

Chemical Name:N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester
CAS No.:742103-00-0
Molecular Formula:C₄₂H₅₃N₃O₈S₃
Molecular Weight:824.096
Hs Code.:

N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Synonyms:N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-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-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-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-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

There total 11 articles about N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-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:

: 229473-27-2
2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose

: 742103-00-0
N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-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: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

2: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

3: 85 percent / aq. iodobenzene diacetate; TEMPO / CH₂Cl₂

4: 73 percent / HOBt; BOP; DiPEA / dimethylformamide

5: iPrSiH; TFA / CH₂Cl₂

6: 468 mg / DiPEA; HOBt; BOP / dimethylformamide

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; 2-propanethiol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-3-yl ester

: 742103-00-0
N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 4.16 g / NaOMe / methanol

2: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

3: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

4: 85 percent / aq. iodobenzene diacetate; TEMPO / CH₂Cl₂

5: 73 percent / HOBt; BOP; DiPEA / dimethylformamide

6: iPrSiH; TFA / CH₂Cl₂

7: 468 mg / DiPEA; HOBt; BOP / dimethylformamide

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium methylate; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; 2-propanethiol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-aminomethyl-tetrahydro-pyran-3-yl ester; hydrochloride

: 742103-00-0
N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-methionine methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂

2: 4.16 g / NaOMe / methanol

3: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

4: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

5: 85 percent / aq. iodobenzene diacetate; TEMPO / CH₂Cl₂

6: 73 percent / HOBt; BOP; DiPEA / dimethylformamide

7: iPrSiH; TFA / CH₂Cl₂

8: 468 mg / DiPEA; HOBt; BOP / dimethylformamide

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium methylate; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; 2-propanethiol; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q