(S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester
• CAS No.: 586413-51-6
• Molecular Formula: C₄₀H₅₀BCl₂N₃O₁₁
• Molecular Weight: 830.568

Synonyms:(S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

Chemical Property of (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

There total 6 articles about (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic 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:

(R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly (391213-72-2) + (S)-2-{[(R)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester; hydrochloride → (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester (586413-51-6)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; at 22 ℃; for 12h;

DOI:10.1021/ja030249r

Reference yield:

isovanillin (621-59-0) → (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester (586413-51-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 0.5 h

2: 98 percent / MgSO₄ / benzene / 24 h

3: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h

4: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

With 1H-imidazole; titanium(IV) isopropylate; 1-hydroxy-7-aza-benzotriazole; chiral amino acid ligand; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; isopropyl alcohol; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja030249r

Reference yield:

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde (97315-18-9) → (S)-2-{[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester (586413-51-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / MgSO₄ / benzene / 24 h

2: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h

3: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

With titanium(IV) isopropylate; 1-hydroxy-7-aza-benzotriazole; chiral amino acid ligand; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; isopropyl alcohol; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja030249r

upstream raw materials:

(R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly

isovanillin

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde diphenylmethyl imine

Downstream raw materials:

C₅₉H₅₃Cl₄N₇O₁₄

C₄₈H₄₄Cl₄IN₅O₁₃

C₄₃H₄₄Cl₂F₃IN₄O₁₀Si

C₄₃H₄₅Cl₂F₃N₄O₁₀Si

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