[(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester
• CAS No.: 247146-51-6
• Molecular Formula: C₃₁H₃₄O₇
• Molecular Weight: 518.607

Synonyms:[(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester

Chemical Property of [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester

There total 13 articles about [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl 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:

(S)-4-Hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-one → [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester (247146-51-6)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / CH₂Cl₂ / 0 °C

2: tetrahydrofuran / -78 - -50 °C

3: 89 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -20 °C

4: 86 percent / (COCl)2; DMSO; Et₃N / -78 °C

5: 89 percent / H₂; AcOH / 10 percent Pd/C / ethyl acetate

6: NaH / toluene / 1.5 h / 23 °C

7: i-Pr₂NEt; DMAP / CH₂Cl₂

8: TBAF / tetrahydrofuran / 0 °C

With 1H-imidazole; triethylsilane; dmap; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 1: silylation / 2: Addition / 3: Reduction / 4: Oxidation / 5: debenzylation / 6: Condensation / 7: Condensation / 8: desilylation;

DOI:10.1021/ja990860j

Reference yield:

(S)-5-Hydroxy-3-oxo-6-triisopropylsilanyloxy-hexanoic acid methyl ester → [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester (247146-51-6)

Guidance literature:

Multi-step reaction with 10 steps

1: Me₄NHB(OAc)3; AcOH / acetonitrile / -35 °C

2: PPTS / benzene / 80 °C

3: imidazole / CH₂Cl₂ / 0 °C

4: tetrahydrofuran / -78 - -50 °C

5: 89 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -20 °C

6: 86 percent / (COCl)2; DMSO; Et₃N / -78 °C

7: 89 percent / H₂; AcOH / 10 percent Pd/C / ethyl acetate

8: NaH / toluene / 1.5 h / 23 °C

9: i-Pr₂NEt; DMAP / CH₂Cl₂

10: TBAF / tetrahydrofuran / 0 °C

With 1H-imidazole; triethylsilane; dmap; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene; 1: Reduction / 2: lactonization / 3: silylation / 4: Addition / 5: Reduction / 6: Oxidation / 7: debenzylation / 8: Condensation / 9: Condensation / 10: desilylation;

DOI:10.1021/ja990860j

Reference yield:

(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one (247146-21-0) → [(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxymethyl-tetrahydro-pyran-(4Z)-ylidene]-acetic acid methyl ester (247146-51-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / H₂; AcOH / 10 percent Pd/C / ethyl acetate

2: NaH / toluene / 1.5 h / 23 °C

3: i-Pr₂NEt; DMAP / CH₂Cl₂

4: TBAF / tetrahydrofuran / 0 °C

With dmap; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 1: debenzylation / 2: Condensation / 3: Condensation / 4: desilylation;

DOI:10.1021/ja990860j

upstream raw materials:

[(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

4,4'-dimethoxytrityl chloride

(2R,6S)-2-Hydroxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

[(2R,6S)-2-Hydroxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Downstream raw materials:

[(2R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

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