(2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

Base Information

Chemical Name:(2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide
CAS No.:865872-75-9
Molecular Formula:C₃₃H₃₈O₉
Molecular Weight:578.659
Hs Code.:

Synonyms:(2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

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Technology Process of (2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

There total 12 articles about (2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide 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: 51.0%

: (2S,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

: 865872-75-9
(2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

Guidance literature:: With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1271/bbb.69.113

Reference yield:

: 865872-73-7
(3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-3-pivaloyloxymethyl-4-butanolide

: 865872-75-9
(2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

Guidance literature:: Multi-step reaction with 4 steps

1.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

1.2: tetrahydrofuran; toluene / 1 h / -70 °C

2.1: KHSO₄ / toluene / 0.5 h / Heating

3.1: 66 percent / OsO₄; 4-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

4.1: 51 percent / CF₃COOH; triethylsilane / CH₂Cl₂ / 16 h / 20 °C

With triethylsilane; potassium hydrogensulfate; osmium(VIII) oxide; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.69.113

Reference yield:

: 868128-07-8
2,2-dimethyl-propionic acid 2-(4-benzyloxy-3-methoxy-phenyl)-5-hydroxy-tetrahydro-furan-3-ylmethyl ester

: 865872-75-9
(2R,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-(3,4-dimethoxybenzyl)-2-hydroxy-3-pivaloyloxymethyl-4-butanolide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 82 percent / pyridinium chlorochrmoate; molecular sieves 4 Angstroem / CH₂Cl₂ / 16 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

2.2: tetrahydrofuran; toluene / 1 h / -70 °C

3.1: KHSO₄ / toluene / 0.5 h / Heating

4.1: 66 percent / OsO₄; 4-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

5.1: 51 percent / CF₃COOH; triethylsilane / CH₂Cl₂ / 16 h / 20 °C

With triethylsilane; potassium hydrogensulfate; osmium(VIII) oxide; 4 A molecular sieve; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.69.113