(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Base Information

Chemical Name:(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine
CAS No.:482331-66-8
Molecular Formula:C₂₅H₃₈N₂O₅
Molecular Weight:446.587
Hs Code.:

Synonyms:(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

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Chemical Property of (3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

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Technology Process of (3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

There total 4 articles about (3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine 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%

: 182368-88-3
(S)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol

: 482331-66-8
(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃; for 12h; to RT;
DOI:10.1016/0040-4039(96)01173-2

Reference yield: 75.0%

: 100-39-0
benzyl bromide

: 182368-88-3
(S)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol

: 482331-66-8
(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Guidance literature:: (S)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol; In tetrahydrofuran; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/S0957-4166(02)00376-2

Reference yield:

: 99603-55-1
(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde

: 482331-66-8
(3R,6S,1'S,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 4 percent / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: tetrahydrofuran / 0.5 h / 0 °C

2.2: 75 percent / Bu₄NI / tetrahydrofuran / 12 h / 20 °C

With n-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1016/S0957-4166(02)00376-2