(2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate

Base Information

• Chemical Name: (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate
• CAS No.: 152615-87-7
• Molecular Formula: C₃₂H₂₄N₂O₇S₂
• Molecular Weight: 612.684
• Mol file: 152615-87-7.mol

Synonyms:(2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate

Chemical Property of (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate

There total 4 articles about (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-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: 49.0%

(2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-oxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate → (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate (152615-87-7)

Guidance literature:

With pyridine; tetraphosphorus decasulfide; In 1,4-dioxane; at 115 ℃; for 2.25h;

DOI:10.1002/jhet.5570300240

Reference yield: 43.0%

(2R,3R,4R)-2-((benzoyloxy)methyl)-5-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate (1333168-18-5) → (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate (152615-87-7)

Guidance literature:

With pyridine; phosphorus pentoxide;

DOI:10.1002/anie.201307064

Reference yield:

methyl 3-amino-4-thiophenecarboxylate hydrochloride (39978-14-8) → (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate (152615-87-7)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium acetate / water / 3.5 h / 20 - 55 °C

2: tin(IV) chloride / nitromethane / 13.17 h / 65 °C / Inert atmosphere

3: hydrogenchloride / methanol; chloroform; water / 2 h / 20 °C

4: triethylamine / ethanol / 16 h / Inert atmosphere; Reflux

5: tetraphosphorus decasulfide / pyridine / 2 h / Inert atmosphere; Reflux

With hydrogenchloride; tetraphosphorus decasulfide; sodium acetate; tin(IV) chloride; triethylamine; In pyridine; methanol; nitromethane; ethanol; chloroform; water; 2: Friedel Crafts alkylation;

DOI:10.1021/ja206095a

upstream raw materials:

methyl 3-amino-4-thiophenecarboxylate hydrochloride

(2R,3R,4R)-2-((benzoyloxy)methyl)-5-(4-oxo-3,4-dihydrothieno[3,4-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate