(4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

Base Information

Chemical Name:(4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one
CAS No.:477807-84-4
Molecular Formula:C₃₅H₄₇NO₈S
Molecular Weight:641.826
Hs Code.:

Synonyms:(4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

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Chemical Property of (4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

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Technology Process of (4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

There total 7 articles about (4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one 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: 92.0%

: 477807-76-4
(4S,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-3-dichloro-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

: 477807-84-4
(4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In benzene; at 78 ℃; for 15h; Heating;
DOI:10.1021/ja026357f

Reference yield:

: 3422-01-3
tert-butyl phenylcarbamate

: 477807-84-4
(4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / -78 - -20 °C

1.2: CuBr*SMe₂ / tetrahydrofuran

1.3: 82 percent / tetrahydrofuran / 0.17 h / -78 °C

2.1: MeLi / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

2.2: 81 percent / tetrahydrofuran; diethyl ether / 3.5 h / -78 - 0 °C

3.1: 78 percent / Zn; CuCl / tetrahydrofuran / 0.25 h / -40 °C

4.1: 92 percent / tri-n-butyltin hydride; Et₃B / benzene / 15 h / 78 °C / Heating

With triethyl borane; methyllithium; tert.-butyl lithium; tri-n-butyl-tin hydride; copper(l) chloride; zinc; In tetrahydrofuran; diethyl ether; pentane; benzene;
DOI:10.1021/ja026357f

Reference yield:

: 18476-63-6
oct-7-yn-4-one

: 477807-84-4
(4R,5R)-4-[2-(N,N-bis-t-butoxycarbonylamino)-phenyl]-4-[2-(2-propyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / p-toluenesulfonic acid / benzene / 24 h / Heating

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 20 °C

2.2: MgBr₂ / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C

2.3: 84 percent / tetrahydrofuran / 0.5 h / -78 °C

3.1: tert-butyllithium / tetrahydrofuran; pentane / -78 - -20 °C

3.2: CuBr*SMe₂ / tetrahydrofuran

3.3: 82 percent / tetrahydrofuran / 0.17 h / -78 °C

4.1: MeLi / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

4.2: 81 percent / tetrahydrofuran; diethyl ether / 3.5 h / -78 - 0 °C

5.1: 78 percent / Zn; CuCl / tetrahydrofuran / 0.25 h / -40 °C

6.1: 92 percent / tri-n-butyltin hydride; Et₃B / benzene / 15 h / 78 °C / Heating

With n-butyllithium; triethyl borane; methyllithium; tert.-butyl lithium; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; copper(l) chloride; zinc; In tetrahydrofuran; diethyl ether; hexane; pentane; benzene;
DOI:10.1021/ja026357f