(2S,3R)-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}-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-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}-3-hydroxy-propionic acid methyl ester
• CAS No.: 143164-87-8
• Molecular Formula: C₆₄H₇₆N₄O₁₅Si
• Molecular Weight: 1169.41
• Mol file: 143164-87-8.mol

Synonyms:

Chemical Property of (2S,3R)-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}-3-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-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}-3-hydroxy-propionic acid methyl ester

There total 46 articles about (2S,3R)-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}-3-hydroxy-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: 71.0%

C67H80N4O15Si (143164-86-7,146388-27-4) → (2R,3S)-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}-3-hydroxy-propionic acid methyl ester (143164-87-8,146388-28-5,146388-33-2) + (2S,3R)-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}-3-hydroxy-propionic acid methyl ester (143164-87-8,146388-28-5,146388-33-2)

Guidance literature:

With acetic acid; In water; at 50 ℃; for 4h;

DOI:10.1055/s-1992-26351

Reference yield: 71.0%

C67H80N4O15Si (143164-86-7,146388-27-4) → (2R,3S)-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}-3-hydroxy-propionic acid methyl ester (143164-87-8,146388-28-5,146388-33-2) + (2S,3R)-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}-3-hydroxy-propionic acid methyl ester (143164-87-8,146388-28-5,146388-33-2)

Guidance literature:

With acetic acid; In water; at 50 ℃; for 4h;

DOI:10.1055/s-1992-26351

Reference yield:

2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid (61172-71-2) → (2R,3S)-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}-3-hydroxy-propionic acid methyl ester (143164-87-8,146388-28-5,146388-33-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) n-BuLi / 1) THF, hexane, -70 deg C, 20 min, 2a) -70 deg C to RT, 2b) RT, 15 h

2: H₂ / <(R)-(RuCl(p-cymene)BINAP>Cl / methanol; CH₂Cl₂ / 72 h / 50 °C / 37503 Torr

3: 97 percent / aq. HOAc / 3 h / 50 °C

4: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h

5: 85 percent / H₂ / (R,R)-BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature

6: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

7: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 15 h / -10 deg C to RT

8: 4 percent / HOAc / H₂O / 4 h / 50 °C

With hydrogenchloride; n-butyllithium; 1,1,3,3-tetramethylguanidine; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ((+)-(1R)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1055/s-1992-26351

upstream raw materials:

C₆₇H₈₀N₄O₁₅Si

2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid

dimethyl 2-(tert-butoxycarbonylamino)malonate

2-benzyloxy-5-bromobenzaldehyde

Downstream raw materials:

(2S,3R)-2-((2S,4R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxy-pentanoylamino)-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonyl-ethyl)-biphenyl-3-yl]-3-hydroxy-propionic acid methyl ester

(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid

(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid methyl ester

(2S,3R)-2-((2S,4R)-2-Amino-5-benzyloxycarbonylamino-4-hydroxy-pentanoylamino)-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonyl-ethyl)-biphenyl-3-yl]-3-hydroxy-propionic acid methyl ester