(3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

Base Information

Chemical Name:(3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one
CAS No.:1426447-34-8
Molecular Formula:C₁₉H₂₆O₄
Molecular Weight:318.413
Hs Code.:

Synonyms:(3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

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Chemical Property of (3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

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Technology Process of (3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

There total 5 articles about (3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one 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: 72.0%

: 1426447-33-7
(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

: 1426447-34-8
(3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

Guidance literature:: (2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid; With (2-methylpropyl)lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - -20 ℃; for 2h; Inert atmosphere;

With monochloromethanesulfonyl chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 2h; Inert atmosphere;

With pyridine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water;
DOI:10.1021/ja4008722

Reference yield:

: 1426447-32-6
(2S,3R,4R,5R,6S)-2-((S)-but-3-en-2-yl)-6-(iodomethyl)-4-((4-methoxybenzyl)oxy)-3,5-dimethyltetrahydro-2H-pyran

: 1426447-34-8
(3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate; osmium(VIII) oxide / water; N,N-dimethyl-formamide; tert-butyl alcohol / 0.08 h / 25 °C / Inert atmosphere

1.2: 6 h / 25 °C

2.1: zinc; ammonium chloride / ethanol / 1 h / Reflux; Inert atmosphere

3.1: (2-methylpropyl)lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / -78 - -20 °C / Inert atmosphere

3.2: 2 h / Inert atmosphere

With osmium(VIII) oxide; (2-methylpropyl)lithium; sodium hydrogencarbonate; ammonium chloride; zinc; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja4008722

Reference yield:

: 1426447-39-3
(2S,3R,4R,5R,6S)-2-((S)-but-3-en-2-yl)-6-(iodomethyl)-3,5-dimethyltetrahydro-2H-pyran-4-ol

: 1426447-34-8
(3R,4S)-4-((2R,3S,4S)-3-((4-methoxybenzyl)oxy)-4-methylhex-5-en-2-yl)-3-methyloxetan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: camphor-10-sulfonic acid / diethyl ether / 30 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; osmium(VIII) oxide / water; N,N-dimethyl-formamide; tert-butyl alcohol / 0.08 h / 25 °C / Inert atmosphere

2.2: 6 h / 25 °C

3.1: zinc; ammonium chloride / ethanol / 1 h / Reflux; Inert atmosphere

4.1: (2-methylpropyl)lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / -78 - -20 °C / Inert atmosphere

4.2: 2 h / Inert atmosphere

With osmium(VIII) oxide; camphor-10-sulfonic acid; (2-methylpropyl)lithium; sodium hydrogencarbonate; ammonium chloride; zinc; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja4008722