Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester
• CAS No.: 215228-40-3
• Molecular Formula: C₃₄H₃₈O₁₅
• Molecular Weight: 686.667

Synonyms:

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-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: 55.0%

(E)-3-[(2R,3S)-2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzo[b]furan-5-yl]-2-propenal (80286-36-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester (215228-40-3)

Guidance literature:

With potassium carbonate; In acetone; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00725-X

Reference yield:

(E)-3-[(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl]-2-propenal (118799-85-2) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester (215228-40-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 5 mg / DIPEA / CH₂Cl₂ / 3 h / Ambient temperature

2: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.5 h

3: 90 percent / aq. HCl / methanol / 3 h

4: 55 percent / K₂CO₃ / acetone / 20 h / Ambient temperature

With hydrogenchloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/S0040-4020(98)00725-X

Reference yield:

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (2R,3S)-7-methoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-3-ylmethyl ester (215228-23-2) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(2R,3S)-3-hydroxymethyl-7-methoxy-5-((E)-3-oxo-propenyl)-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester (215228-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.5 h

2: 90 percent / aq. HCl / methanol / 3 h

3: 55 percent / K₂CO₃ / acetone / 20 h / Ambient temperature

With hydrogenchloride; potassium carbonate; In tetrahydrofuran; methanol; acetone;

DOI:10.1016/S0040-4020(98)00725-X

upstream raw materials:

(E)-3-[(2R,3S)-2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzo[b]furan-5-yl]-2-propenal

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

(E)-3-[(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl]-2-propenal

(E)-3-[(2R,3S)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3'-methoxy-4'-methoxymethoxyphenyl)-1-benzo[b]furan-5-yl]-2-propenal

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