(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

Base Information

Chemical Name:(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine
CAS No.:247186-19-2
Molecular Formula:C₂₅H₃₂N₂O₃
Molecular Weight:408.541
Hs Code.:

Synonyms:(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

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Chemical Property of (2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

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Technology Process of (2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

There total 1 articles about (2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine 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: 69.0%

: 1700-31-8
3-benzyloxybenzyl bromide

: 110117-71-0
(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine

: (2R,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

: 247186-19-2
(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

Guidance literature:: (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

3-benzyloxybenzyl bromide; In tetrahydrofuran;
DOI:10.1002/(SICI)1521-3773(19990816)38:16<2443::AID-ANIE2443>3.0.CO;2-B

Reference yield: 71.0%

: 247186-19-2
(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

: (S)-2-Amino-3-(3-benzyloxy-phenyl)-propionic acid ethyl ester

Guidance literature:: With hydrogenchloride; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1021/ja021327y

Reference yield:

: 247186-19-2
(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

: (13E,15E)-(3S,6S,21S)-3-(3-hydroxybenzyl)-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

Guidance literature:: Multi-step reaction with 13 steps

1: 71 percent / aq. HCl / acetonitrile / 2 h / 20 °C

2: 8.85 g / tetrahydrofuran / -15 - 20 °C

3: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / 0 °C

4: N-methylmorpholine / tetrahydrofuran / 0.5 h / -10 °C

5: 780 mg / N-methylmorpholine / tetrahydrofuran / -10 - 20 °C

6: H₂ / 10 percent Pd/C / propan-2-ol / 5 h

7: 5.4 g / imidazole / dimethylformamide / 16 h / 40 °C

8: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

9: 2.98 g / tetrahydrofuran / 20 °C

10: Zn; aq. NH₄OAc / tetrahydrofuran / 20 °C

11: 230 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

12: 47 percent / (PCy)3Cl₂Ru=CHPh / CH₂Cl₂ / 40 °C

13: 75 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; Grubbs catalyst first generation; trimethylsilyl trifluoromethanesulfonate; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 11: Mitsunobu reaction;
DOI:10.1021/ja021327y