2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

Base Information

Chemical Name:2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran
CAS No.:476461-13-9
Molecular Formula:C₁₆H₁₉BrO₄
Molecular Weight:355.228
Hs Code.:

Synonyms:2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

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Chemical Property of 2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

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Technology Process of 2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

There total 5 articles about 2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran 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: 94.0%

: 824-94-2
p-methoxybenzyl chloride

: 476461-12-8
2-(S)-(2,2-dibromovinyl)-6-(S)-methoxytetrahydropyran-4-(R)-ol

: 476461-13-9
2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

Guidance literature:: 2-(S)-(2,2-dibromovinyl)-6-(S)-methoxytetrahydropyran-4-(R)-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

p-methoxybenzyl chloride; With sodium iodide; In tetrahydrofuran; at 20 ℃; for 22.5h; Further stages.;
DOI:10.1021/ol0201557

Reference yield:

: 91312-68-4
methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-oxo-α-D-erythro-hexopyranoside

: 476461-13-9
2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine; zinc / CH₂Cl₂ / 22 °C

1.2: 63 percent / triphenylphosphine; zinc / CH₂Cl₂ / 22 °C

2.1: 88 percent / HF / acetonitrile; H₂O / 0.67 h / 0 °C

3.1: sodium hydride / tetrahydrofuran; various solvent(s) / 1.5 h / 0 °C

3.2: 94 percent / sodium iodide / tetrahydrofuran; various solvent(s) / 22.5 h / 20 °C

With hydrogen fluoride; sodium hydride; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ol0201557

Reference yield:

: 91312-61-7
methyl 3-O-(tert-butyldimethylsilyl)-2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexapyranoside

: 476461-13-9
2-(S)-bromoethynyl-6-(S)-methoxy-4-(R)-(4-methoxybenzyloxy)-tetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: Na / diethyl ether; liquid ammonia / 0.83 h / -78 - 22 °C

1.2: 98 percent / ammonium chloride / diethyl ether / 12 h / 22 °C

2.1: 98 percent / DMSO; (COCl)2; ET₃N / CH₂Cl₂ / 2.33 h / -78 - 22 °C

3.1: triphenylphosphine; zinc / CH₂Cl₂ / 22 °C

3.2: 63 percent / triphenylphosphine; zinc / CH₂Cl₂ / 22 °C

4.1: 88 percent / HF / acetonitrile; H₂O / 0.67 h / 0 °C

5.1: sodium hydride / tetrahydrofuran; various solvent(s) / 1.5 h / 0 °C

5.2: 94 percent / sodium iodide / tetrahydrofuran; various solvent(s) / 22.5 h / 20 °C

With oxalyl dichloride; hydrogen fluoride; sodium; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; ammonia; water; acetonitrile; 2.1: Swern oxidation;
DOI:10.1021/ol0201557