(2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester
• CAS No.: 260354-46-9
• Molecular Formula: C₄₂H₅₂N₂O₇Si
• Molecular Weight: 724.97
• Mol file: 260354-46-9.mol

Synonyms:(2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Chemical Property of (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

There total 13 articles about (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid 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: 73.0%

O-tert-butyldiphenylsilyl-L-threonine methyl ester (148205-40-7) + (S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione (260354-45-8) → (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (260354-46-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo990964c

Reference yield:

Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine (1025887-95-9) → (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (260354-46-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 91 percent / H₂ / Pd/C / methanol / 16 h / 20 °C / 760.05 Torr

3: 98 percent / TEMPO; KBr; NaOCl / CH₂Cl₂; H₂O; aq. phosphate buffer / 3 h / 0 °C / pH 7.0

4: 73 percent / CH₂Cl₂ / 24 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; triethylamine; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; water; 1: Cycloaddition / 2: Hydrogenation / 3: cycloexpansion / 4: Acylation;

DOI:10.1021/jo990964c

Reference yield:

(2R,3S)-methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (122517-81-1) → (2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (260354-46-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / p-TsOH*H₂O / benzene / 1 h / Heating

2: DIBAL / toluene / 2 h / -78 °C

3: CH₂Cl₂ / 1 h / 0 °C

4: Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 91 percent / H₂ / Pd/C / methanol / 16 h / 20 °C / 760.05 Torr

6: 98 percent / TEMPO; KBr; NaOCl / CH₂Cl₂; H₂O; aq. phosphate buffer / 3 h / 0 °C / pH 7.0

7: 73 percent / CH₂Cl₂ / 24 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; water; toluene; benzene; 1: Cycloaddition / 2: Reduction / 3: Condensation / 4: Cycloaddition / 5: Hydrogenation / 6: cycloexpansion / 7: Acylation;

DOI:10.1021/jo990964c

upstream raw materials:

O-tert-butyldiphenylsilyl-L-threonine methyl ester

(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine

3-(4-methoxy-phenyl)acrylic acid methyl ester

Downstream raw materials:

(2S,3R)-2-{(S)-2-Amino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester