(S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate

Base Information

• Chemical Name: (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate
• CAS No.: 1354913-10-2
• Molecular Formula: C₃₃H₃₉NO₅Si
• Molecular Weight: 557.762

Synonyms:(S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate

Chemical Property of (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate

There total 6 articles about (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate 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: 74.0%

(S,E)-4-(((tert-butyl)diphenylsilyl)oxy)-2-methylpent-2-enal (1354913-32-8) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → (S,2E,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate (1370463-11-8) + (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate (1354913-10-2)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 0 - 20 ℃; for 96h;

DOI:10.1039/c1ob06559a

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (S,2E,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate (1370463-11-8) + (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate (1354913-10-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

3.1: dichloromethane / 18 h / 20 °C

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate / dichloromethane; water / 0.17 h / 20 °C

5.2: 5 h / 20 °C

6.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 96 h / 0 - 20 °C

With 1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; N,N,N',N'-tetramethylguanidine; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: Wittig olefination / 6.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/c1ob06559a

Reference yield:

methyl (S,E)-4-(tert-butyldiphenylsilyloxy)-2-methylpent-2-en-1-ol (1040132-14-6) → (S,2E,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate (1370463-11-8) + (S,2Z,4E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhepta-2,4-dienoate (1354913-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate / dichloromethane; water / 0.17 h / 20 °C

1.2: 5 h / 20 °C

2.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 96 h / 0 - 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate; N,N,N',N'-tetramethylguanidine; In dichloromethane; water; 2.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/c1ob06559a

upstream raw materials:

methyl (S,E)-4-(tert-butyldiphenylsilyloxy)-2-methylpent-2-en-1-ol

(S,E)-4-(((tert-butyl)diphenylsilyl)oxy)-2-methylpent-2-enal

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

(S,E)-ethyl 4-(tert-butyldiphenylsilyloxy)-2-methylpent-2-enoate

Downstream raw materials:

(2S,6S,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-(carbamoyloxy)-4-methylhept-4-enoate

(2S,4R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-4-(tert-butoxycarbonylamino)-4-methylhept-5-enoate

(2S,4R)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)-amino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4-methylpentanoate

(2S,6S,E)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butyl-diphenylsilyloxy)-4-methylhept-4-enoate

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