[(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester
• CAS No.: 79308-58-0
• Molecular Formula: C₁₆H₂₂O₇S
• Molecular Weight: 358.412

Synonyms:[(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

Chemical Property of [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

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Technology Process of [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

There total 5 articles about [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl 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: 86.0%

[(4S,5R)-4-(Toluene-4-sulfonyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-acetic acid ethyl ester (79308-57-9) → [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester (79308-58-0)

Guidance literature:

With palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1016/S0040-4039(01)90546-5

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester (79308-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / tetrahydrofuran / 6 h / Heating

2: sodium ethoxide / ethanol / 1 h

3: 80 percent / 4-(N,N-dimethylamino)pyridine / pyridine

4: 4-(N,N-dimethylamino)pyridine / pyridine / 20 h / 55 °C

5: 86 percent / 10percent Pd/C / ethanol; ethyl acetate

With dmap; palladium on activated charcoal; sodium ethanolate; In tetrahydrofuran; pyridine; ethanol; ethyl acetate;

DOI:10.1016/S0040-4039(01)90546-5

Reference yield:

ethyl 2,3,4-trideoxy-D-ribo-hept-2-enoate (79308-40-0) → [(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester (79308-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium ethoxide / ethanol / 1 h

2: 80 percent / 4-(N,N-dimethylamino)pyridine / pyridine

3: 4-(N,N-dimethylamino)pyridine / pyridine / 20 h / 55 °C

4: 86 percent / 10percent Pd/C / ethanol; ethyl acetate

With dmap; palladium on activated charcoal; sodium ethanolate; In pyridine; ethanol; ethyl acetate;

DOI:10.1016/S0040-4039(01)90546-5

upstream raw materials:

[(4S,5R)-4-(Toluene-4-sulfonyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-acetic acid ethyl ester

2-deoxy-D-ribose

ethyl 2,3,4-trideoxy-D-ribo-hept-2-enoate

ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate

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