(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

Base Information

Chemical Name:(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran
CAS No.:916154-05-7
Molecular Formula:C₂₁H₃₂O₄Si
Molecular Weight:376.568
Hs Code.:

Synonyms:(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

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Chemical Property of (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

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Technology Process of (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

There total 7 articles about (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran 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: 80.0%

: 916154-04-6
((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol

: 1779-49-3
Methyltriphenylphosphonium bromide

: 916154-05-7
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

Guidance literature:: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol; With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 2h;
DOI:10.1021/acs.orglett.1c03723

Reference yield: 71.0%

: 4-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carbaldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 916154-05-7
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

Guidance literature:: 4-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carbaldehyde; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 2h;

Methyltriphenylphosphonium bromide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.5h;

Reference yield:

: 913258-74-9
3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal

: 916154-05-7
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: 78 percent / HF; pyridine / tetrahydrofuran / 0 - 20 °C

2.1: oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 75 percent / n-BuLi / CH₂Cl₂; hexane; tetrahydrofuran / 2 h / 20 °C

With pyridine; oxalyl dichloride; hydrogen fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1021/jo0615504