N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Base Information

Chemical Name:N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester
CAS No.:104213-53-8
Molecular Formula:C₄₄H₆₅N₅O₁₄Si
Molecular Weight:916.111
Hs Code.:

N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Synonyms:N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

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Chemical Property of N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

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Technology Process of N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

There total 32 articles about N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline 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: 86.0%

: (2S,3S,4S)-1-{(2S,3R)-2-[(2S,3R)-2-Amino-3-hydroxy-4-(4-hydroxy-phenyl)-butyrylamino]-3-hydroxy-butyryl}-3-hydroxy-4-methyl-pyrrolidine-2-carboxylic acid methyl ester; compound with trifluoro-acetic acid

: 104197-70-8
N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-proline

: 104213-53-8
N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Guidance literature:: With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; for 16h; ice/water cooling bath;
DOI:10.1021/ja00257a041

Reference yield: 72.0%

: 104197-70-8
N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-proline

: 3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

: 104213-53-8
N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Guidance literature:: With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1021/ja00279a065

Reference yield:

: 19728-63-3
N-benzyloxycarbonyl-L-treonine

: 104213-53-8
N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 92 percent / PPh₃ / CH₂Cl₂ / 14 h / Ambient temperature

3: 1) 1-(trimethylsilyl)imidazole, NEt₃ / 1) DMF, 2.5 h, RT, 2) RT, 16 h

4: 72 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 2 h

With 1H-imidazole; diethylphosphoryl cyanide; triethylamine; 1-(Trimethylsilyl)imidazole; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87959-X