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

Base Information

• Chemical Name: (5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid
• CAS No.: 892397-07-8
• Molecular Formula: C₃₅H₃₉NO₅Si
• Molecular Weight: 581.784
• Mol file: 892397-07-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid 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: 96.0%

(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) → (5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid (892397-07-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 36h;

DOI:10.1021/ol060677c

Reference yield:

(2S,3R)-methyl 2-amino-3-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate (892397-17-0) → (5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid (892397-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaHCO₃ / ethyl acetate; H₂O / 14 h / 20 °C

2: 96 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 36 h / 20 °C

With lithium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; water; ethyl acetate;

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)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid (892397-07-8)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 96 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 36 h / 20 °C

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

DOI:10.1021/ol060677c

upstream raw materials:

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

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

(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:

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

(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

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

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate