acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 931421-45-3
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384
• Mol file: 931421-45-3.mol

Synonyms:acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

There total 3 articles about acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 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: 82.0%

acetic acid 4,5-dihydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester (931421-44-2) + allyl bromide (106-95-6) → acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester (931421-45-3)

Guidance literature:

acetic acid 4,5-dihydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester; With di(n-butyl)tin oxide; In toluene; Heating;

allyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2006.11.032

Reference yield:

acetic acid 6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (931421-64-6) → acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester (931421-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / aq. HOAc / 40 °C

2.1: Bu₂SnO / toluene / Heating

2.2: 82 percent / CsF / dimethylformamide / 20 °C

With di(n-butyl)tin oxide; acetic acid; In toluene;

DOI:10.1016/j.bmcl.2006.11.032

Reference yield:

1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside (693788-18-0) → acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester (931421-45-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / pyridine / 20 °C

2.1: 85 percent / aq. HOAc / 40 °C

3.1: Bu₂SnO / toluene / Heating

3.2: 82 percent / CsF / dimethylformamide / 20 °C

With pyridine; di(n-butyl)tin oxide; acetic acid; In toluene;

DOI:10.1016/j.bmcl.2006.11.032

upstream raw materials:

acetic acid 4,5-dihydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

allyl bromide

acetic acid 6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside

Downstream raw materials:

acetic acid 4-allyloxy-2-(4-methoxy-benzyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

acetic acid 4-(2-hydroxy-ethoxy)-2-(4-methoxy-benzyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

4-methoxy-benzoic acid 2-(3-acetoxy-2-trichloroacetimidoyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-ethyl ester

4-methoxy-benzoic acid 2-[3-acetoxy-2-(4-methoxy-benzyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-ethyl ester