(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

Base Information

Chemical Name:(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester
CAS No.:212388-36-8
Molecular Formula:C₃₃H₃₈N₂O₇
Molecular Weight:574.674
Hs Code.:

Synonyms:(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

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Chemical Property of (2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

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Technology Process of (2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

There total 12 articles about (2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester 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:

: 100-39-0
benzyl bromide

: 441020-34-4
(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid

: 212388-36-8
(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

Guidance literature:: With caesium carbonate; Yield given. Multistep reaction; 1.) EtOH, 2.) DMF, RT, 12 h;
DOI:10.1021/ja980489k

Reference yield:

: 89711-08-0
N-(t-butoxycarbonyl)glycinal

: 212388-36-8
(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: tetrahydrofuran / 2 h / -30 °C / Inert atmosphere

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 8 h / 20 °C / Inert atmosphere

3: lithium hydroxide; water / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide / diethyl ether / 12 h / Inert atmosphere; Reflux

5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C

6: potassium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; copper(l) iodide; palladium 10% on activated carbon; water; hydrogen; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jacs.1c02382

Reference yield:

: 134676-36-1,1267551-72-3
(2-Hydroxy-but-3-enyl)-carbamic acid tert-butyl ester

: 212388-36-8
(2S,5R)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 8 h / 20 °C / Inert atmosphere

2: lithium hydroxide; water / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide / diethyl ether / 12 h / Inert atmosphere; Reflux

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C

5: potassium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; copper(l) iodide; palladium 10% on activated carbon; water; hydrogen; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jacs.1c02382