(3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluoro-dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluoro-dihydrofuran-2(3H)-one
• CAS No.: 1355049-97-6
• Molecular Formula: C19H19FO4
• Molecular Weight: 330.356
• Mol file: 1355049-97-6.mol

Synonyms:(3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluoro-dihydrofuran-2(3H)-one;2-Deoxy-2-fluoro-3,5-bis-O-(phenylmethyl)-D-ribonic acid gamma-lactone

Chemical Property of (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluoro-dihydrofuran-2(3H)-one

Chemical Property:

• Boiling Point: 472.5±45.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 3.05210

Purity/Quality:

≥99% ^*data from raw suppliers

(3R,4R,5R)-4-Benzyloxy-5-(benzyloxymethyl)-3-fluoro-tetrahydrofuran-2-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3R,?4R,?5R)?-?4-?(Benzyloxy)?-?5-?((benzyloxy)?methyl)?-?3-?fluorodihydrofuran-?2(3H)?-?one is a reagent used in the preparation of Favipiravir analogues used in the treatment of influenza.

Technology Process of (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluoro-dihydrofuran-2(3H)-one

There total 3 articles about (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluoro-dihydrofuran-2(3H)-one 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: 95.0%

(3R,4R,5R)-4-benzyloxy-5-(benzyloxymethyl)-3-fluorotetrahydrofuran-2-ol → (3R,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-fluorodihydrofuran-2(3H)-one (1355049-97-6)

Guidance literature:

With dipyridinium dichromate; In dichloromethane;

DOI:10.1021/acs.jmedchem.5b01933

Reference yield:

methyl 3,5-di-O-benzyl-2-deoxy-2-fluoro-α/β-D-ribofuranoside (863642-44-8) → (3R,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-fluorodihydrofuran-2(3H)-one (1355049-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid; water / 20 °C

2: dipyridinium dichromate / dichloromethane / 20 °C / Molecular sieve

With dipyridinium dichromate; water; trifluoroacetic acid; In dichloromethane;

Reference yield:

→ (3R,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-fluorodihydrofuran-2(3H)-one (1355049-97-6)

Guidance literature:

With acetic anhydride; In dimethyl sulfoxide; at 20 ℃; for 48h; Inert atmosphere;

upstream raw materials:

methyl 3,5-di-O-benzyl-2-deoxy-2-fluoro-α/β-D-ribofuranoside

Downstream raw materials:

(3R,4R,5R)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluorotetrahydrofuran-2-ol

C₂₆H₂₇FN₄O₃

(3R,4R,5R)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluorotetrahydrofuran-2-ol

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