acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester

Base Information

• Chemical Name: acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester
• CAS No.: 681811-43-8
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 681811-43-8.mol

Synonyms:acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester

Chemical Property of acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester

There total 7 articles about acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester 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: 86.0%

(2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-ol (681811-42-7) + acetic anhydride (108-24-7) → acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester (681811-43-8)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2003.12.002

Reference yield:

dithiocarbonic acid O-(6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl) ester S-methyl ester → acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester (681811-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.82 g / Et₃B; nBu₃SnH / benzene; hexane / 3 h / 20 °C

2: 75 percent / p-TsOH / 20 °C

3: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

With pyridine; dmap; triethyl borane; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In hexane; benzene;

DOI:10.1016/j.bmc.2003.12.002

Reference yield:

(-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (14048-35-2) → acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester (681811-43-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: nBu₂SnO / toluene / 2 h / 140 - 150 °C

1.2: 73 percent / nBu₄NBr / toluene / 90 - 100 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: tetrahydrofuran / 1 h / 20 °C

3.1: 1.82 g / Et₃B; nBu₃SnH / benzene; hexane / 3 h / 20 °C

4.1: 75 percent / p-TsOH / 20 °C

5.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

With pyridine; dmap; triethyl borane; tri-n-butyl-tin hydride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; toluene; benzene;

DOI:10.1016/j.bmc.2003.12.002

upstream raw materials:

(2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-ol

acetic anhydride

(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

(-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

N-[1-((2R,3R,4S)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl]benzamide

acetic acid (2R,3R,4S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-benzyloxymethyltetrahydrofuran-3-yl ester