(3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

Base Information

• Chemical Name: (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate
• CAS No.: 1402821-77-5
• Molecular Formula: C₂₈H₂₂BrNO₇
• Molecular Weight: 564.389

Synonyms:(3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

Chemical Property of (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

There total 3 articles about (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-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:

(2R,3R,4S)-2-((R)-1-(benzoyloxy)ethyl)-5-cyanotetrahydrofuran-3,4-diyldibenzoate (1402821-76-4) → (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate (1402821-77-5)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; at 75 ℃; for 5h; UV-irradiation;

DOI:10.1080/15257770.2015.1075550

Reference yield:

1-O-Acetyl-2,3,5-tri-O-benzoyl-6-deoxy-β-D-allofuranose (72159-45-6) → (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate (1402821-77-5)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / nitromethane / 0.75 h / 20 °C

2: N-Bromosuccinimide / tetrachloromethane / 5 h / 75 °C / UV-irradiation

With N-Bromosuccinimide; boron trifluoride diethyl etherate; In tetrachloromethane; nitromethane;

DOI:10.1080/15257770.2015.1075550

Reference yield:

→ (3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate (1402821-77-5)

Guidance literature:

upstream raw materials:

1-O-Acetyl-2,3,5-tri-O-benzoyl-6-deoxy-β-D-allofuranose

(2R,3R,4S)-2-((R)-1-(benzoyloxy)ethyl)-5-cyanotetrahydrofuran-3,4-diyldibenzoate

Downstream raw materials:

(2R,3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-cyano-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

(R)-1-((2R,3S,4R,5R)-3-(benzoyloxy)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxytetrahydrofuran-2-yl)ethyl benzoate

(S)-1-((2R,3R,4R,5R)-3-(benzoyloxy)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)ethyl benzoate

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