4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol

Base Information

• Chemical Name: 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol
• CAS No.: 852310-60-2
• Molecular Formula: C₁₃H₁₈O₅
• Molecular Weight: 254.283
• Mol file: 852310-60-2.mol

Synonyms:4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol

Chemical Property of 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol

There total 6 articles about 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol 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: 87.0%

6-(4-methoxybenzyloxy)-2,2,5-trimethyl-(3aS,5S,6R,6aS)-perhydrofurol[2,3-d][1,3]dioxole (852310-58-8) → 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol (852310-60-2)

Guidance literature:

With sulfuric acid; acetic acid; In water;

DOI:10.1016/j.tetlet.2005.02.140

Reference yield:

2,2,5-trimethyl-(3aS,5S,6R,6aS)-perhydrofurol[2,3-d][1,3]dioxol-6-ol (852310-59-9) → 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol (852310-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaH; Bu₄NI / dimethylformamide

2: 83 percent / aq. HCl; aq. AcOH / 40 °C

With hydrogenchloride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2007.06.017

Reference yield:

6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole (218621-71-7) → 4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol (852310-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / LiAlH₄ / diethyl ether

2: 98 percent / NaH; Bu₄NI / dimethylformamide

3: 83 percent / aq. HCl; aq. AcOH / 40 °C

With hydrogenchloride; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2007.06.017

upstream raw materials:

6-(4-methoxybenzyloxy)-2,2,5-trimethyl-(3aS,5S,6R,6aS)-perhydrofurol[2,3-d][1,3]dioxole

2,2,5-trimethyl-(3aS,5S,6R,6aS)-perhydrofurol[2,3-d][1,3]dioxol-6-ol

6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole

p-Methoxybenzyl bromide

Downstream raw materials:

Methanesulfonic acid (E)-(1S,2S)-2-(4-methoxy-benzyloxy)-4-(4-methoxy-phenyl)-1-methyl-but-3-enyl ester

1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene

3-(4-methoxybenzyloxy)-5-(4-methoxyphenyl)-(2S,3S,4E)-4-penten-2-ol

2-(4-methoxybenzyloxy)-4-(4-methoxyphenyl)-1-methyl-(1S,2S,3E)-3-butenyl formate