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

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoic acid
• CAS No.: 183609-73-6
• Molecular Formula: C₃₀H₅₁NO₇Si
• Molecular Weight: 565.823

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about (S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoic acid 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) → (S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoic acid (183609-73-6)

Guidance literature:

Multi-step reaction with 6 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

With n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; hydrogen; sodium hydride; magnesium; dimethyl sulfoxide; 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) → (S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoic acid (183609-73-6)

Guidance literature:

Multi-step reaction with 6 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

With n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; hydrogen; sodium hydride; magnesium; dimethyl sulfoxide; 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) → (S)-2-Benzyloxycarbonylamino-7-((4S,5S)-2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)-heptanoic acid (183609-73-6)

Guidance literature:

Multi-step reaction with 5 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

With n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; hydrogen; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja9615841

upstream raw materials:

((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester

[(4S,5S)-5-(4-Bromo-butyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-triisopropyl-silane

triisopropylsilyl chloride

2,3-O-isopropylidene-L-threitol

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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