(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

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Chemical Name:(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione
CAS No.:923293-48-5
Molecular Formula:C₃₄H₃₈BrN₅O₅
Molecular Weight:676.61
Hs Code.:

Synonyms:(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

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Chemical Property of (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

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Technology Process of (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

There total 6 articles about (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione 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: 81.0%

: 923293-47-4
(3S,6S)-1-allyl-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]piperazine-2,5-dione

: 923293-48-5
(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

Guidance literature:: (3S,6S)-1-allyl-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]piperazine-2,5-dione; With borane-THF; In tetrahydrofuran; at -40 - 20 ℃; for 17h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;
DOI:10.1021/jo0619635

Reference yield:

: N-propargyl-O-benzyl-L-serine methyl ester

: 923293-48-5
(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 72 percent / ethyldiisopropylamine; HATU / CH₂Cl₂ / 0 - 20 °C

2.1: 78 percent / H₂O / 0.22 h / 20 - 200 °C / microwave irradiation

3.1: 94 percent / BEMP / dimethylformamide / 0.5 h / 60 °C / microwave irradiation

4.1: 95 percent / sodium ascorbate; copper(II) sulfate pentahydrate / CH₂Cl₂; H₂O / 20 h / 20 °C

5.1: BH₃*THF complex / tetrahydrofuran / 17 h / -40 - 20 °C

5.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

With borane-THF; copper(II) sulfate; sodium L-ascorbate; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0619635

Reference yield:

: 923293-39-4
cyclo-(4-bromo-L-phenylalanyl-N-propargyl-O-benzyl-L-serinyl)

: 923293-48-5
(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / BEMP / dimethylformamide / 0.5 h / 60 °C / microwave irradiation

2.1: 95 percent / sodium ascorbate; copper(II) sulfate pentahydrate / CH₂Cl₂; H₂O / 20 h / 20 °C

3.1: BH₃*THF complex / tetrahydrofuran / 17 h / -40 - 20 °C

3.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

With borane-THF; copper(II) sulfate; sodium L-ascorbate; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0619635