(2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

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Chemical Name:(2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate
CAS No.:220243-90-3
Molecular Formula:C₃₆H₄₇BrI₄N₂O₁₀
Molecular Weight:1255.3
Hs Code.:

Synonyms:(2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

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Chemical Property of (2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

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Technology Process of (2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

There total 5 articles about (2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate 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: 28.0%

: 220243-88-9
(2S)-tert-butyl 6-bromo-2-[(tert-butoxycarbonyl)amino]-5-hydroxyhexanoate

: O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxine

: 220243-91-4
(2S,5S)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

: 220243-90-3
(2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1016/S0040-4020(98)01023-0

Reference yield:

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

: 220243-90-3
(2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 4-N-methylmorpholine / tetrahydrofuran / 0.42 h / 0 °C

2: tetrahydrofuran; diethyl ether / 3 h / 0 °C

3: 5.76 g / aq. HBr / diethyl ether / 0.42 h / -20 °C

4: 77 percent / NaBH₄ / methanol / 3 h / 0 - 20 °C

5: 28 percent / 1,3-dicyclohexyl carbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

With 4-methyl-morpholine; dmap; sodium tetrahydroborate; hydrogen bromide; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Acylation / 2: Acylation / 3: Substitution / 4: Reduction / 5: Esterification;
DOI:10.1016/S0040-4020(98)01023-0

Reference yield:

: (S)-2-tert-Butoxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid tert-butyl ester

: 220243-90-3
(2S,5R)-(-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-6-bromo-5-[O-methoxy-N-(tert-butoxycarbonyl)-L-thyroxinyl]-hexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: tetrahydrofuran; diethyl ether / 3 h / 0 °C

2: 5.76 g / aq. HBr / diethyl ether / 0.42 h / -20 °C

3: 77 percent / NaBH₄ / methanol / 3 h / 0 - 20 °C

4: 28 percent / 1,3-dicyclohexyl carbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

With dmap; sodium tetrahydroborate; hydrogen bromide; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Acylation / 2: Substitution / 3: Reduction / 4: Esterification;
DOI:10.1016/S0040-4020(98)01023-0