Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 850430-48-7
• Molecular Formula: C₂₂H₂₈O₁₀
• Molecular Weight: 452.458

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-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: 93.0%

4-methoxy-phenol (150-76-5) + 1,2,4,6-Tetra-O-acetyl-3-O-allyl-β-D-glucopyranose (197005-21-3) → Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester (850430-48-7)

Guidance literature:

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane;

DOI:10.1039/c5ra16659d

Reference yield: 70.0%

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside (39698-00-5) + 4-methoxy-phenol (150-76-5) → Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester (850430-48-7)

Guidance literature:

With tetramethylammonium trifluoromethanesulphonate; In dichloromethane; at 0 ℃;

DOI:10.1055/s-2004-837221

Reference yield: 93.0%

Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-allyloxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester (850430-48-7) → (2R,3R,4S,5R,6S)-4-Allyloxy-2-hydroxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3,5-diol

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1039/c5ra16659d

upstream raw materials:

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

4-methoxy-phenol

1,2,4,6-Tetra-O-acetyl-3-O-allyl-β-D-glucopyranose

Downstream raw materials:

(2R,4aR,6S,7R,8R,8aR)-8-Allyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

2-Azidomethyl-benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-5-hydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

2-Azidomethyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-hydroxy-2-(4-methoxy-phenoxy)-6-(4-oxo-pentanoyloxymethyl)-tetrahydro-pyran-3-yl ester

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