methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate

Base Information

• Chemical Name: methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate
• CAS No.: 901273-08-3
• Molecular Formula: C₃₄H₃₇NO₈
• Molecular Weight: 587.67
• Mol file: 901273-08-3.mol

Synonyms:

Chemical Property of methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate

There total 4 articles about methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate 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:

1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-methylnaphthalene (901273-00-5) → methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate (901273-08-3)

Guidance literature:

Multi-step reaction with 3 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

With N-Bromosuccinimide; 1,1,3,3-tetramethylguanidine; sodium hydrogencarbonate; dimethyl sulfoxide; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; 2: Kornblum reaction / 3: Horner-Emmons olefination reaction;

DOI:10.1002/ejoc.200500835

Reference yield:

1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-(bromomethyl)naphthalene (901273-02-7) → methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate (901273-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaHCO₃; DMSO / 3 h / 95 °C

2: 81 percent / tetramethylguanidine / tetrahydrofuran / 7 h / -78 - 20 °C

With 1,1,3,3-tetramethylguanidine; sodium hydrogencarbonate; dimethyl sulfoxide; In tetrahydrofuran; 1: Kornblum reaction / 2: Horner-Emmons olefination reaction;

DOI:10.1002/ejoc.200500835

Reference yield:

t-butyl malonate (541-16-2) → methyl (Z)-2-(benzyloxycarbonylamino)-3-{4-[2',2'-bis(tert-butoxycarbonyl)vinyl]}naphthylacrylate (901273-08-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / TiCl₄; pyridine / CCl₄; tetrahydrofuran / 4 h / 0 - 20 °C

2: 95 percent / N-bromosuccinimide; dibenzoyl peroxide / CCl₄ / Heating

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

4: 81 percent / tetramethylguanidine / tetrahydrofuran / 7 h / -78 - 20 °C

With pyridine; N-Bromosuccinimide; 1,1,3,3-tetramethylguanidine; titanium tetrachloride; sodium hydrogencarbonate; dimethyl sulfoxide; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; 1: Knoevenagel condensation reaction / 3: Kornblum reaction / 4: Horner-Emmons olefination reaction;

DOI:10.1002/ejoc.200500835

upstream raw materials:

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

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

t-butyl malonate

4-methyl-1-naphthaldehyde

Downstream raw materials:

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

Refernces