((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 237410-10-5
• Molecular Formula: C₁₃H₁₅FO₅
• Molecular Weight: 270.258

Synonyms:((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate

Chemical Property of ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

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Technology Process of ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate

There total 16 articles about ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate 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: 62.0%

((2R,3R,4R,5R)-3,4-dihydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate → ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate (237410-10-5) + methyl 2,3-anhydro-5-O-benzoyl-β-D-ribofuranoside

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at 20 ℃; for 19h;

DOI:10.1080/15257779908041542

Reference yield: 52.0%

sodium benzoate (532-32-1) + Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-fluoro-2-methoxy-tetrahydro-furan-3-yl ester (551929-56-7) → methyl 2,5-di-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside (112695-36-0) + ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate (237410-10-5)

Guidance literature:

With 18-crown-6 ether; In dimethyl sulfoxide; at 200 ℃; for 13h;

DOI:10.1016/S0960-894X(03)00027-1

Reference yield: 24.0%

(3,4-dihydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate → 5-O-benzoyl-2-O-methyl-3-deoxy-3-fluoro-α-D-arabinofuranosyl fluoride + ((2R,3S,4S,5R)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate (237410-10-5) + methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside (237410-14-9) + ((2R,3S,4S,5S)-3-fluoro-4-hydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate (237410-13-8)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at 24 - 26 ℃; for 18h;

DOI:10.1016/j.tet.2019.02.027

upstream raw materials:

dimethyl sulfoxide

sodium benzoate

Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-fluoro-2-methoxy-tetrahydro-furan-3-yl ester

Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside

Downstream raw materials:

methyl 2,5-di-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside

Benzoic acid (2R,3R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-5-methoxy-tetrahydro-furan-2-ylmethyl ester

((2R,3R,4S)-5-acetoxy-4-(benzoyloxy)-3-fluorotetrahydrofuran-2-yl)methyl benzoate

(2R,3S,4S,5R)-4-Benzoyloxy-3-fluoro-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester

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