(2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Base Information

• Chemical Name: (2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate
• CAS No.: 141846-58-4
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.429
• DSSTox Substance ID: DTXSID30451086
• Mol file: 141846-58-4.mol

Synonyms:22837-37-2;(2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate;[(2S,3R)-5-methoxy-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate;(2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)-tetrahydrofuran-3-yl 4-methylbenzoate;SCHEMBL4988218;DTXSID30451086;(2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl4-methylbenzoate;(2S,3R)-5-methoxy-2-[(4-methylbenzoyloxy)methyl]oxolan-3-yl 4-methylbenzoate

Chemical Property of (2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 384.15728848
• Heavy Atom Count: 28
• Complexity: 519

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)OC)OC(=O)C3=CC=C(C=C3)C
• Isomeric SMILES: CC1=CC=C(C=C1)C(=O)OC[C@H]2[C@@H](CC(O2)OC)OC(=O)C3=CC=C(C=C3)C

Technology Process of (2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

There total 9 articles about (2S,3R)-5-Methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 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: 100.0%

4-methyl-benzoyl chloride (874-60-2) + (2S,3R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol (446251-73-6) → 1-methoxy-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose (141846-58-4)

Guidance literature:

With triethylamine; In acetone; at 20 ℃; for 20h;

Reference yield:

methanol (67-56-1) + 2-deoxy-3,5-di-O-p-toluoyl-L-ribofuranose → 1-methoxy-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose (141846-58-4)

Guidance literature:

methanol; With hydrogenchloride; acetyl chloride; at 5 - 20 ℃; for 0.666667h;

2-deoxy-3,5-di-O-p-toluoyl-L-ribofuranose; In methanol; at 10 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/op0500436

Reference yield:

D-xylono-1,4-lactone (15384-37-9) → 1-methoxy-2-deoxy-3,5-di-O-p-methylbenzeneformyl-L-ribofuranose (141846-58-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen bromide / acetic acid / 3 h / 20 - 45 °C

1.2: 0 - 20 °C

2.1: sodium iodide; trifluoroacetic acid / Isopropyl acetate / 6 h / 20 - 85 °C

3.1: potassium hydroxide / water / 3.5 h / 15 - 80 °C / pH Ca_. 14

3.2: Amberlite IR-120 (plus) ion-exchange acidic resin / 1 h / 20 °C / pH 3

4.1: pyridine / 1,2-dimethoxyethane / 3.83 h / 0 - 5 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / 1,2-dimethoxyethane; hexane / 1.25 h / -60 °C / Inert atmosphere

6.1: hydrogenchloride; acetyl chloride / 0.67 h / 5 - 20 °C

6.2: 3 h / 10 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; hydrogen bromide; diisobutylaluminium hydride; acetyl chloride; trifluoroacetic acid; sodium iodide; potassium hydroxide; In 1,2-dimethoxyethane; hexane; Isopropyl acetate; water; acetic acid;

DOI:10.1021/op0500436

upstream raw materials:

4-methyl-benzoyl chloride

(2S,3R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol

D-Xylose

methanol

Downstream raw materials:

3,5-di-O-(4-methylbenzoyl)-2-deoxy-α-L-erythro-pentofuranosyl chloride