2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester

Base Information

• Chemical Name: 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester
• CAS No.: 218915-06-1
• Molecular Formula: C₅₄H₇₄N₄O₁₁Si
• Molecular Weight: 983.287

Synonyms:2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester

Chemical Property of 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester

Chemical Property:

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Safty Information:

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Technology Process of 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester

There total 16 articles about 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic 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: 81.0%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-2-{(2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionylamino}-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester (218915-05-0) → 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester (218915-06-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2714::AID-ANIE2714>3.0.CO;2-#

Reference yield:

Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn-OH (28252-50-8) → 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester (218915-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / K₂CO₃ / dimethylformamide / 12 h / 25 °C

2: 99 percent / H₂ / 20 percent Pd(OH)2 / methanol / 1 h / 25 °C

3: 82 percent / HOAt; EDC / tetrahydrofuran / 0 - 25 °C

4: 81 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; hydrogen; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Hydrogenolysis / 3: Acylation / 4: Etherification;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

Z-Asn(Mbh)-OMe (28252-54-2) → 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester (218915-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / 20 percent Pd(OH)2 / methanol / 1 h / 25 °C

2: 82 percent / HOAt; EDC / tetrahydrofuran / 0 - 25 °C

3: 81 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrogenolysis / 2: Acylation / 3: Etherification;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-2-{(2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionylamino}-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester

Asn(Mbh)-OMe

N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn-OH

Downstream raw materials:

C₅₈H₇₉Br₂ClN₈O₁₁Si

N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionylamino]-succinamic acid methyl ester

N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionylamino]-succinamic acid

N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionylamino]-succinamic acid methyl ester

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