Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester
• CAS No.: 461666-80-8
• Molecular Formula: C₂₃H₃₀O₁₃
• Molecular Weight: 514.483

Synonyms:Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-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: 32.0%

2,3,5-tri-O-acetyl-α,β-L-arabinofuranosyl trichloroacetimidate + 4'-methoxyphenyl α-L-arabinofuranoside (461666-79-5) → Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester (461666-80-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -42 ℃; for 1h;

DOI:10.1055/s-2002-31893

Reference yield:

1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) → Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester (461666-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / BF₃*Et₂O / 12 h / 0 °C

2: 73 percent / NaOCH₃ / methanol / 12 h / 20 °C

3: 32 percent / TMSOTf / CH₂Cl₂ / 1 h / -42 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1055/s-2002-31893

Reference yield:

4-methoxy-phenol (150-76-5) → Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester (461666-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / BF₃*Et₂O / 12 h / 0 °C

2: 73 percent / NaOCH₃ / methanol / 12 h / 20 °C

3: 32 percent / TMSOTf / CH₂Cl₂ / 1 h / -42 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1055/s-2002-31893

upstream raw materials:

4'-methoxyphenyl α-L-arabinofuranoside

1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose

4-methoxy-phenol

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

Downstream raw materials:

Acetic acid (2S,3S,4R,5S)-4-acetoxy-2-((2R,3R,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxymethyl)-5-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester

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