N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine
• CAS No.: 901273-15-2
• Molecular Formula: C₃₃H₃₇NO₈
• Molecular Weight: 575.659
• Mol file: 901273-15-2.mol

Synonyms:N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine

Chemical Property of N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine

There total 7 articles about N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine 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: 90.0%

methyl N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)]vinyl}naphthyl)-L-alaninate (901273-11-8) → N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine (901273-15-2)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃; for 16h;

DOI:10.1002/ejoc.200500835

Reference yield:

4-[2',2'-bis(tert-butoxycarbonyl)vinyl]naphthaldehyde (901273-05-0) → N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine (901273-15-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / tetramethylguanidine / tetrahydrofuran / 7 h / -78 - 20 °C

2: 90 percent / H₂; bis(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate; (S,S)-Me-DuPHOS / methanol / 24 h / 7600 Torr

3: 90 percent / aq. Na₂CO₃ / methanol / 16 h / 20 °C

With bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; 1,1,3,3-tetramethylguanidine; hydrogen; sodium carbonate; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; In tetrahydrofuran; methanol; 1: Horner-Emmons olefination reaction;

DOI:10.1002/ejoc.200500835

Reference yield:

1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-methylnaphthalene (901273-00-5) → N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthyl)-L-alanine (901273-15-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / N-bromosuccinimide; dibenzoyl peroxide / CCl₄ / Heating

2: 85 percent / NaHCO₃; DMSO / 3 h / 95 °C

3: 81 percent / tetramethylguanidine / tetrahydrofuran / 7 h / -78 - 20 °C

4: 90 percent / H₂; bis(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate; (S,S)-Me-DuPHOS / methanol / 24 h / 7600 Torr

5: 90 percent / aq. Na₂CO₃ / methanol / 16 h / 20 °C

With N-Bromosuccinimide; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; 1,1,3,3-tetramethylguanidine; hydrogen; sodium hydrogencarbonate; sodium carbonate; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; dimethyl sulfoxide; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; 2: Kornblum reaction / 3: Horner-Emmons olefination reaction;

DOI:10.1002/ejoc.200500835

upstream raw materials:

methyl N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)]vinyl}naphthyl)-L-alaninate

1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-methylnaphthalene

4-[2',2'-bis(tert-butoxycarbonyl)vinyl]naphthaldehyde

1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-(bromomethyl)naphthalene

Refernces