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

Base Information

Chemical Name:methyl N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)]vinyl}naphthyl)-L-alaninate
CAS No.:901273-11-8
Molecular Formula:C₃₄H₃₉NO₈
Molecular Weight:589.686
Hs Code.:

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

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

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

There total 5 articles about methyl N-(benzyloxycarbonyl)-β-(1-{4-[2',2'-bis(tert-butoxycarbonyl)]vinyl}naphthyl)-L-alaninate 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:

: 901273-00-5
1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-methylnaphthalene

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

Guidance literature:: Multi-step reaction with 4 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

With N-Bromosuccinimide; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; 1,1,3,3-tetramethylguanidine; hydrogen; sodium hydrogencarbonate; 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

Reference yield:

: 901273-05-0
4-[2',2'-bis(tert-butoxycarbonyl)vinyl]naphthaldehyde

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

Guidance literature:: Multi-step reaction with 2 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

With bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; 1,1,3,3-tetramethylguanidine; hydrogen; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; In tetrahydrofuran; methanol; 1: Horner-Emmons olefination reaction;
DOI:10.1002/ejoc.200500835

Reference yield:

: 901273-02-7
1-[2',2'-bis(tert-butoxycarbonyl)vinyl]-4-(bromomethyl)naphthalene

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 90 percent / H₂; bis(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate; (S,S)-Me-DuPHOS / methanol / 24 h / 7600 Torr

With bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; 1,1,3,3-tetramethylguanidine; hydrogen; sodium hydrogencarbonate; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; dimethyl sulfoxide; In tetrahydrofuran; methanol; 1: Kornblum reaction / 2: Horner-Emmons olefination reaction;
DOI:10.1002/ejoc.200500835