(5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate

Base Information

• Chemical Name: (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate
• CAS No.: 892397-18-1
• Molecular Formula: C₃₆H₄₁NO₅Si
• Molecular Weight: 595.811
• Mol file: 892397-18-1.mol

Synonyms:(5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate

Chemical Property of (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate

There total 4 articles about (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate 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: 91.0%

(2S,3R)-methyl 2-amino-3-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate (892397-17-0) + benzyl chloroformate (501-53-1,94274-21-2) → (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate (892397-18-1)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 14h;

DOI:10.1021/ol060677c

Reference yield:

(6R,7S)-methyl 6-benzyl-2,2,11,11-tetramethyl-9-oxo-3,3-diphenyl-4,10-dioxa-8-aza-3-siladodecane-7-carboxylate (892397-16-9) → (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate (892397-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / trifluoroacetic acid; thioanisole / CH₂Cl₂ / 0.67 h / 17 °C

2: 91 percent / NaHCO₃ / ethyl acetate; H₂O / 14 h / 20 °C

With methyl-phenyl-thioether; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; water; ethyl acetate;

DOI:10.1021/ol060677c

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (5S,6R)-methyl 6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylate (892397-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide / 36 h / 20 °C

2: 99 percent / trifluoroacetic acid; thioanisole / CH₂Cl₂ / 0.67 h / 17 °C

3: 91 percent / NaHCO₃ / ethyl acetate; H₂O / 14 h / 20 °C

With 1H-imidazole; methyl-phenyl-thioether; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol060677c

upstream raw materials:

(2S,3R)-methyl 2-amino-3-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate

benzyl chloroformate

(6R,7S)-methyl 6-benzyl-2,2,11,11-tetramethyl-9-oxo-3,3-diphenyl-4,10-dioxa-8-aza-3-siladodecane-7-carboxylate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid

(4R,5R)-methyl 2-((5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecan-5-yl)-5-methyl-4,5-dihydrooxazole-4-carboxylate

(2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)]