(2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS No.: 1352744-35-4
• Molecular Formula: C₃₄H₃₀O₁₀S
• Molecular Weight: 630.672

Synonyms:(2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property of (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate

There total 7 articles about (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate 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: 85.0%

2,5-anhydro-3,4,6-tri-O-benzoyl-D-mannitol (1146544-48-0) + p-toluenesulfonyl chloride (98-59-9) → (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate (1352744-35-4)

Guidance literature:

With pyridine; In chloroform; at 0 - 20 ℃;

DOI:10.1002/cjoc.201300489

Reference yield: 80.0%

((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate (1352744-34-3) + benzoyl chloride (98-88-4) → (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate (1352744-35-4)

Guidance literature:

With pyridine; at 22 ℃; Cooling with ice;

DOI:10.1016/j.tet.2011.10.067

Reference yield:

2,5-anhydro-D-mannitol (41107-82-8) → (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate (1352744-35-4)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; pyridine / 72 h / 45 °C

2: pyridine / 0 - 20 °C

3: acetic acid / water / 6 h / 45 °C

4: pyridine / chloroform / 0 - 20 °C

With pyridine; dmap; acetic acid; In chloroform; water;

DOI:10.1002/cjoc.201300489

upstream raw materials:

((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate

benzoyl chloride

p-toluenesulfonyl chloride

2,5-anhydro-3,4,6-tri-O-benzoyl-D-mannitol

Downstream raw materials:

1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

2,5-anhydro-3,4,6-tri-O-benzoyl-1-fluoro-D-mannitol

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