tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

Base Information

Chemical Name:tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate
CAS No.:408341-58-2
Molecular Formula:C₃₀H₄₆N₂O₁₀
Molecular Weight:594.703
Hs Code.:

Synonyms:tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

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Chemical Property of tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

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Technology Process of tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

There total 7 articles about tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate 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: 88.0%

: 408341-57-1
tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate

: 408341-58-2
tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

Guidance literature:: With hydrogen; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In methanol; for 24h; under 3620.04 Torr;
DOI:10.1055/s-2002-19295

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 408341-58-2
tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / DMAP / acetonitrile / 18 h / 20 °C

2: 91 percent / DIBAL / hexane; diethyl ether / 0.25 h / -78 °C

3: 91 percent / DBU / CH₂Cl₂ / 5.5 h / 20 °C

4: 88 percent / H₂ / [Rh(I)(COD)(S,S)-Et-DuPHOS][OTf] / methanol / 24 h / 3620.04 Torr

With dmap; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In methanol; diethyl ether; hexane; dichloromethane; acetonitrile; 3: Horner-Emmons olefination;
DOI:10.1055/s-2002-19295

Reference yield:

: 24277-39-2
N-tert-butoxycarbonyl glutamic acid tert-butyl ester

: 408341-58-2
tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / DCC; DMAP; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

2: 89 percent / DMAP / acetonitrile / 18 h / 20 °C

3: 91 percent / DIBAL / hexane; diethyl ether / 0.25 h / -78 °C

4: 91 percent / DBU / CH₂Cl₂ / 5.5 h / 20 °C

5: 88 percent / H₂ / [Rh(I)(COD)(S,S)-Et-DuPHOS][OTf] / methanol / 24 h / 3620.04 Torr

With dmap; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In methanol; diethyl ether; hexane; dichloromethane; acetonitrile; 4: Horner-Emmons olefination;
DOI:10.1055/s-2002-19295