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

Base Information

• Chemical Name: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol
• CAS No.: 916154-04-6
• Molecular Formula: C₂₀H₃₂O₅Si
• Molecular Weight: 380.557
• Mol file: 916154-04-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol 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: 91.0%

tert-butyl(((2R,4aR,8R,8aR)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)dimethylsilane (340320-92-5) → ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol (916154-04-6)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -20 - 20 ℃; for 0.333333h; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201203284

Reference yield: 84.0%

3-O-tert-butyldimethylsilyl-4,6-O-(4-methoxybenzylidene)-D-(-)-glucal (384346-91-2) → ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol (916154-04-6)

Guidance literature:

3-O-tert-butyldimethylsilyl-4,6-O-(4-methoxybenzylidene)-D-(-)-glucal; With diisobutylaluminium hydride; In dichloromethane; at -15 - 20 ℃; for 2.33333h;

With water; Rochelle's salt; In methanol; dichloromethane; ethyl acetate; at 0 ℃; for 1h;

Reference yield: 78.0%

3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal (913258-74-9) → ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol (916154-04-6)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo0615504

upstream raw materials:

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

p-methoxybenzyl chloride

tert-butyl(((2R,4aR,8R,8aR)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)dimethylsilane

Downstream raw materials:

C₂₁H₃₆O₆Si