3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl

Base Information

• Chemical Name: 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl
• CAS No.: 121125-11-9
• Molecular Formula: C₅₇H₆₄N₂O₁₀Si
• Molecular Weight: 965.228

Synonyms:3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl

Chemical Property of 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl

Chemical Property:

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Technology Process of 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl

There total 20 articles about 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl 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: 100.0%

(E)-2-Benzyloxycarbonylamino-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-biphenyl-3-yl]-acrylic acid 2-trimethylsilanyl-ethyl ester (121125-08-4,121125-09-5) → 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl (121125-11-9)

Guidance literature:

With hydrogen; (R,R)-⁺BF4^-; In methanol; for 72h; under 2250.2 Torr; Ambient temperature;

DOI:10.1055/s-1992-26293

Reference yield: 66.0%

2(S)-benzyloxycarbonylamino-3-(2-benzyloxy-5-iodophenyl)propionic acid (2-trimethylsilyl)ethyl ester (616888-59-6) + benzyl 3-[2-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2(S)-tert-butoxycarbonylaminopropionate (636594-72-4) → 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl (121125-11-9)

Guidance literature:

2(S)-benzyloxycarbonylamino-3-(2-benzyloxy-5-iodophenyl)propionic acid (2-trimethylsilyl)ethyl ester; With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 20 - 40 ℃;

benzyl 3-[2-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2(S)-tert-butoxycarbonylaminopropionate; In N,N-dimethyl-formamide; at 40 - 50 ℃; for 6.5h; Product distribution / selectivity;

Reference yield:

2-benzyloxy-5-bromobenzaldehyde (121124-94-5) → 3-<(S)-2-Benzyloxycarbonylamino-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-tert-butoxycarbonylamino)-2-(benzyloxycarbonyl)ethyl>-4,4'-dibenzyloxybiphenyl (121125-11-9)

Guidance literature:

Multi-step reaction with 6 steps

1: KOtBu / CH₂Cl₂ / 14 h / -60 - 20 °C

2: Irradiation

3: H₂ / (+) / methanol / 72 h / 20 °C

5: KOtBu / CH₂Cl₂ / 14 h / -60 - 20 °C

6: H₂ / (+) / methanol / 72 h / 20 °C

With potassium tert-butylate; hydrogen; (+); In methanol; dichloromethane;

upstream raw materials:

(E)-2-Benzyloxycarbonylamino-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-biphenyl-3-yl]-acrylic acid 2-trimethylsilanyl-ethyl ester

2-benzyloxy-5-bromobenzaldehyde

2-(2-(benzyloxy)-5-bromophenyl)-1,3-dioxane

Benzyl 2-tert-butoxycarbonylamino-2-(dimethoxyphosphoryl)acetate

Downstream raw materials:

(S)-3-[3'-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-4,4'-bis-benzyloxy-biphenyl-3-yl]-2-benzyloxycarbonylamino-propionic acid 2-trimethylsilanyl-ethyl ester

2-(Trimethylsilyl)ethyl 3-[3'-(2(S)-amino-2-benzyloxycarbonylethyl)4,4'-bisbenzyloxybiphenyl-3-yl]-2(S)-benzyloxycarbonylaminopropionate hydrochloride

(S)-2-((2S,4R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxy-pentanoylamino)-3-{4,4'-bis-benzyloxy-3'-[(S)-2-benzyloxycarbonylamino-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-biphenyl-3-yl}-propionic acid benzyl ester

C₇₃H₈₄N₄O₁₄Si

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