Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester

Base Information

• Chemical Name: Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester
• CAS No.: 705971-58-0
• Molecular Formula: C₁₈H₁₈O₄S
• Molecular Weight: 330.405

Synonyms:Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester

Chemical Property of Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester

Chemical Property:

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Technology Process of Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester

There total 5 articles about Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] 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: 71.0%

benzoyl chloride (98-88-4) + 1',2'-dideoxy-1'β-(4-mercaptophenyl)-D-ribofuranose (705971-56-8) → Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester (705971-58-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 4 ℃;

DOI:10.1016/j.bmcl.2004.03.015

Reference yield:

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose (4330-34-1) → Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester (705971-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / tin(IV) chloride / CH₂Cl₂ / 8 h / -15 °C

2: 37 percent / LiAlH₄ / tetrahydrofuran / 1 h / 4 °C

3: 71 percent / diisopropylethylamine / tetrahydrofuran / 1 h / 20 °C

With lithium aluminium tetrahydride; tin(IV) chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Friedel-Crafts alkylation;

DOI:10.1016/j.tet.2004.12.038

Reference yield:

diphenyldisulfane (882-33-7) → Thiobenzoic acid S-[4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-phenyl] ester (705971-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / tin(IV) chloride / CH₂Cl₂ / 8 h / -15 °C

2: 37 percent / LiAlH₄ / tetrahydrofuran / 1 h / 4 °C

3: 71 percent / diisopropylethylamine / tetrahydrofuran / 1 h / 20 °C

With lithium aluminium tetrahydride; tin(IV) chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Friedel-Crafts alkylation;

DOI:10.1016/j.tet.2004.12.038

upstream raw materials:

benzoyl chloride

1',2'-dideoxy-1'β-(4-mercaptophenyl)-D-ribofuranose

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

diphenyldisulfane

Downstream raw materials:

Thiobenzoic acid S-(4-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-phenyl) ester

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