Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

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Chemical Name:Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
CAS No.:721448-99-3
Molecular Formula:C₁₉H₁₈O₆
Molecular Weight:342.348
Hs Code.:

Synonyms:Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

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Chemical Property of Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

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Technology Process of Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

There total 9 articles about Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl 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: 98.0%

: 721448-97-1
acetic acid 4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

: 721448-99-3
Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

Guidance literature:: With pyridine hydrogenfluoride; In pyridine; dichloromethane; at 20 ℃; for 113h;
DOI:10.1016/j.bmcl.2004.02.097

Reference yield:

: 19311-91-2
N,N-diethylsalicylamide

: 721448-99-3
Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

2.1: s-BuLi; N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran / 1.5 h / -40 °C

2.2: tetrahydrofuran / 17 h / -40 - -30 °C

2.3: NaH / tetrahydrofuran / 3 h / 70 °C

3.1: K₂CO₃ / methanol / 3 h / 70 °C

4.1: 85 percent / K₂CO₃ / acetone / 19 h / 20 °C

5.1: 94 percent / HF*Py / pyridine; CH₂Cl₂ / 20 °C

6.1: imidazole / dimethylformamide / 2 h / 0 °C

7.1: 64 percent / Et₃N; DMAP / CH₂Cl₂

8.1: 98 percent / HF*Py / pyridine; CH₂Cl₂ / 113 h / 20 °C

With 1H-imidazole; dmap; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; potassium carbonate; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmcl.2004.02.097

Reference yield:

: 100-39-0
benzyl bromide

: 721448-99-3
Acetic acid (S)-4-benzyloxy-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / K₂CO₃ / acetone / 19 h / 20 °C

2: 94 percent / HF*Py / pyridine; CH₂Cl₂ / 20 °C

3: imidazole / dimethylformamide / 2 h / 0 °C

4: 64 percent / Et₃N; DMAP / CH₂Cl₂

5: 98 percent / HF*Py / pyridine; CH₂Cl₂ / 113 h / 20 °C

With 1H-imidazole; dmap; potassium carbonate; pyridine hydrogenfluoride; triethylamine; In pyridine; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmcl.2004.02.097