acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 929016-73-9
• Molecular Formula: C₂₂H₂₈O₁₂
• Molecular Weight: 484.457

Synonyms:acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

There total 3 articles about acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-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: 86.1%

2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (42344-69-4) → acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester (929016-73-9)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol; at 25 ℃; for 1h;

DOI:10.1080/07328300600966497

Reference yield:

isovanillin (621-59-0) → acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester (929016-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68.4 percent / aq. KOH; DMAP / CH₂Cl₂ / 5 h / Heating

2: 86.1 percent / NaBH₄ / propan-2-ol / 1 h / 25 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; In dichloromethane; isopropyl alcohol;

DOI:10.1080/07328300600966497

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester (929016-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68.4 percent / aq. KOH; DMAP / CH₂Cl₂ / 5 h / Heating

2: 86.1 percent / NaBH₄ / propan-2-ol / 1 h / 25 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; In dichloromethane; isopropyl alcohol;

DOI:10.1080/07328300600966497

upstream raw materials:

2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

isovanillin

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 4-methoxy-3-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester

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