Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-hydroxy-phenoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-hydroxy-phenoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 114882-14-3
• Molecular Formula: C₂₀H₂₄O₁₁
• Molecular Weight: 440.404

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

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

Chemical Property:

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

There total 3 articles about Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-hydroxy-phenoxy)-tetrahydro-pyran-4-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: 85.6%

2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose (78942-86-6) + recorcinol (108-46-3) → Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-hydroxy-phenoxy)-tetrahydro-pyran-4-yl ester (114882-14-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 0.833333h;

DOI:10.1080/00397919208021347

Reference yield: 10.0%

recorcinol (108-46-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Tetraacetyl-(3-acetoxy-phenyl)-β-D-glucosid (15921-66-1) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-hydroxy-phenoxy)-tetrahydro-pyran-4-yl ester (114882-14-3) + 1,3-Bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene (85708-07-2) + 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose (3366-47-0)

Guidance literature:

With sodium perchlorate; In acetonitrile; Further byproducts given; Electrolysis; Ag cathode; background current;

DOI:10.1039/a901329f

Reference yield:

2,3,4,6-tetraacetylglucose (3947-62-4,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,6207-76-7) → Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-hydroxy-phenoxy)-tetrahydro-pyran-4-yl ester (114882-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃COONa

2: 85.6 percent / BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -20 °C

With boron trifluoride diethyl etherate; sodium 2,2,2-trifluoroacetate; In dichloromethane;

DOI:10.1080/00397919208021347

upstream raw materials:

2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose

recorcinol

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

2,3,4,6-tetraacetylglucose

Downstream raw materials:

1,3-bis-β-D-glucopyranosyloxy-benzene

resorcinol-O-β-D-glucoside

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