(R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 183609-99-6
• Molecular Formula: C₅₄H₇₈N₄O₁₀Si
• Molecular Weight: 971.32

Synonyms:(R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester

There total 11 articles about (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic 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:

triisopropylsilyl chloride (13154-24-0) → (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (183609-99-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, 3 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, RT, 1 h

3: 1.) nBuLi / 1.) THF, -23 deg C, 1 h, 2.) THF, a) -78 deg C, 30 min, b) 0 deg C, 45 min

4: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h

5: 97 percent / PPh₃, CBr₄ / tetrahydrofuran / 0.5 h / Ambient temperature

6: 1.) Mg, 1,2-dibromoethane, 2.) CuBr*Me₂S / 1.) Et₂O, 160 min, 2.) THF, Et₂O, -23 deg C, 140 min

7: 1.) N-methylmorpholine, 2.) 1-hydroxybenzotriazole, 3.) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

With 4-methyl-morpholine; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; hydrogen; sodium hydride; benzotriazol-1-ol; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylene dibromide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja9615841

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (183609-99-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, 3 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, RT, 1 h

3: 1.) nBuLi / 1.) THF, -23 deg C, 1 h, 2.) THF, a) -78 deg C, 30 min, b) 0 deg C, 45 min

4: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h

5: 97 percent / PPh₃, CBr₄ / tetrahydrofuran / 0.5 h / Ambient temperature

6: 1.) Mg, 1,2-dibromoethane, 2.) CuBr*Me₂S / 1.) Et₂O, 160 min, 2.) THF, Et₂O, -23 deg C, 140 min

7: 1.) N-methylmorpholine, 2.) 1-hydroxybenzotriazole, 3.) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

With 4-methyl-morpholine; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; hydrogen; sodium hydride; benzotriazol-1-ol; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylene dibromide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja9615841

Reference yield:

((4S,5S)-2,2-dimethyl-5-(((triisopropylsilyl)oxy)methyl)-1,3-dioxolan-4-yl)methanol (183609-61-2) → (R)-1-((S)-2-{(S)-2-[(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (183609-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, RT, 1 h

2: 1.) nBuLi / 1.) THF, -23 deg C, 1 h, 2.) THF, a) -78 deg C, 30 min, b) 0 deg C, 45 min

3: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h

4: 97 percent / PPh₃, CBr₄ / tetrahydrofuran / 0.5 h / Ambient temperature

5: 1.) Mg, 1,2-dibromoethane, 2.) CuBr*Me₂S / 1.) Et₂O, 160 min, 2.) THF, Et₂O, -23 deg C, 140 min

6: 1.) N-methylmorpholine, 2.) 1-hydroxybenzotriazole, 3.) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

With 4-methyl-morpholine; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; hydrogen; benzotriazol-1-ol; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylene dibromide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja9615841

upstream raw materials:

methyl (R)-1-{(S)-2-[(S)-2-amino-3-phenylpropanamido]-3-phenylpropanoyl}pyrrolidine-2-carboxylate

(S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoic acid

triisopropylsilyl chloride

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

Toluene-4-sulfonic acid (4S,5S)-5-[5-((5S,8S,11S,13aR)-5,8-dibenzyl-4,7,10,13-tetraoxo-tetradecahydro-3a,6,9,12-tetraaza-cyclopentacyclododecen-11-yl)-pentyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(R)-1-((S)-2-{(S)-2-[(S)-2-Amino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoylamino]-3-phenyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid

Toluene-4-sulfonic acid (2S,3S)-8-((5S,8S,11S,13aR)-5,8-dibenzyl-4,7,10,13-tetraoxo-tetradecahydro-3a,6,9,12-tetraaza-cyclopentacyclododecen-11-yl)-2,3-dihydroxy-octyl ester

C₃₆H₄₇⁽³⁾HN₄O₇

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