(5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

Base Information

Chemical Name:(5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester
CAS No.:433711-81-0
Molecular Formula:C₂₆H₄₀N₂O₇
Molecular Weight:492.613
Hs Code.:

Synonyms:(5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

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Chemical Property of (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

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Technology Process of (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

There total 9 articles about (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl 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: 95.0%

: 623-47-2
propynoic acid ethyl ester

: 335693-80-6
C₂₁H₃₄N₂O₅

: 433711-81-0
(5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

Guidance literature:: propynoic acid ethyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

C₂₁H₃₄N₂O₅; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ja0126226

Reference yield:

: 176108-62-6
(R)-4-but-3-enoyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 433711-81-0
(5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / H₂ / Pd/C / methanol / 14 h / 20 °C / atmospheric pressure

2.1: 92 percent / tetrahydrofuran / -78 - 20 °C

3.1: 99 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 20 °C

4.1: 90 percent / p-TsOH; methanol / 0.5 h / 20 °C

5.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 2 h / 20 °C

6.1: 90 percent / MgSO₄ / CH₂Cl₂ / 4 h / 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 95 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

With methanol; n-butyllithium; pyridine-SO₃ complex; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Parikh-Doering oxidation;
DOI:10.1021/ja0126226

Reference yield:

: 167102-62-7,1822572-30-4
(R)-N,O-isopropylidenyl-2-(N-tert-butyloxycarbonylamino)-3-oxo-propanamide-N,O-dimethyl-hydroxyamine

: 433711-81-0
(5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / tetrahydrofuran / 1 h / -65 °C

2.1: 99 percent / H₂ / Pd/C / methanol / 14 h / 20 °C / atmospheric pressure

3.1: 92 percent / tetrahydrofuran / -78 - 20 °C

4.1: 99 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 20 °C

5.1: 90 percent / p-TsOH; methanol / 0.5 h / 20 °C

6.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 2 h / 20 °C

7.1: 90 percent / MgSO₄ / CH₂Cl₂ / 4 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: 95 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

With methanol; n-butyllithium; pyridine-SO₃ complex; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Parikh-Doering oxidation;
DOI:10.1021/ja0126226