(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
• Mol file: 916154-05-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol (916154-04-6) + Methyltriphenylphosphonium bromide (1779-49-3) → (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran (916154-05-7)

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 + Methyltriphenylphosphonium bromide (1779-49-3) → (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran (916154-05-7)

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:

3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal (913258-74-9) → (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran (916154-05-7)

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

upstream raw materials:

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

Methyltriphenylphosphonium bromide

3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal

1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

Downstream raw materials:

(2R,3S,4R)-3-(4-methoxybenzyloxy)-2-vinyl-3,4-dihydro-2H-pyran-4-ol

(1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde