((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol

Base Information

• Chemical Name: ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol
• CAS No.: 183722-51-2
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Mol file: 183722-51-2.mol

Synonyms:((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol

Chemical Property of ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol

There total 10 articles about ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-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: 83.0%

tert-butyl(((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)-methoxy)diphenylsilane → ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol (183722-51-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1080/00397911.2015.1043018

Reference yield: 80.0%

(4aR,8aS)-2-(4-Methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (183722-50-1) → ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol (183722-51-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -40 ℃; for 5h;

DOI:10.1002/1521-3773(20011203)40:23<4441::AID-ANIE4441>3.0.CO;2-I

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol (183722-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 10-camphorsulfonic acid / acetonitrile / 10 h / 25 °C

2: 80 percent / diisobutylaluminum hydride / tetrahydrofuran / 5 h / -40 °C

With (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; acetonitrile;

DOI:10.1002/1521-3773(20011203)40:23<4441::AID-ANIE4441>3.0.CO;2-I

upstream raw materials:

(4aR,8aS)-2-(4-Methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

(2R,3S)-2-hydroxymethyltetrahydropyran-3-ol

4-methoxy-benzaldehyde

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(2S,3S)-3-(4-Methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

2-[(2R,3S)-3-(4-Methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-ethanol

[(2R,3S)-3-(4-Methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-acetic acid

((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-acetic acid (2R,4aR,6S,7R,8aS)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester