N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide

Base Information

• Chemical Name: N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide
• CAS No.: 914652-59-8
• Molecular Formula: C₄₂H₄₅INO₄PSi
• Molecular Weight: 813.787
• Mol file: 914652-59-8.mol

Synonyms:N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide

Chemical Property of N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide

There total 1 articles about N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide 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: 63.0%

N-[5-(tert-butyldiphenylsilanyloxy)-2-tributyltinyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide → N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide (914652-59-8)

Guidance literature:

With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 0.0666667h;

DOI:10.1002/adsc.200505171

Reference yield: 86.0%

N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide (914652-59-8) + phenylmagnesium bromide → N-[5-(tert-butyldiphenylsilanyloxy)-2-phenyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2E)-enyl]-P,P-diphenylphosphinamide (914652-61-2)

Guidance literature:

phenylmagnesium bromide; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; at 55 - 60 ℃; for 4h;

DOI:10.1002/adsc.200505171

Reference yield:

N-[5-(tert-butyldiphenylsilanyloxy)-2-iodo-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2Z)-enyl]-P,P-diphenylphosphinamide (914652-59-8) → 4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester (914652-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ZnCl₂ / tetrahydrofuran; diethyl ether / 0 - 20 °C

1.2: 86 percent / Pd(PPh₃)4 / tetrahydrofuran; diethyl ether / 4 h / 55 - 60 °C

2.1: HCl / methanol / 20 °C

2.2: NaHCO₃ / ethyl acetate; H₂O / 0.25 h

2.3: 79 percent / ethyl acetate; H₂O / 2 h / 0 °C

With hydrogenchloride; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; 1.2: Negishi coupling;

DOI:10.1002/adsc.200505171

Downstream raw materials:

N-[5-(tert-butyldiphenylsilanyloxy)-2-phenyl-(4R)-methyl-(1SR)-(4-methoxycarbonyl-phenyl)pent-(2E)-enyl]-P,P-diphenylphosphinamide

4-[(1SR)-benzyloxycarbonylamino-2-iodo-(4R)-methyl-5-oxopent-(2Z)-enyl]benzoic acid methyl ester

4-[(1SR)-benzyloxycarbonylamino-(4R)-carboxy-2-iodopent-(2Z)-enyl]benzoic acid methyl ester

4-[(1SR)-benzyloxycarbonylamino-5-hydroxy-(4R)-methyl-2-phenylpent-(2E)-enyl]benzoic acid methyl ester