(4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

Base Information

Chemical Name:(4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester
CAS No.:152401-21-3
Molecular Formula:C₄₂H₅₀O₁₁
Molecular Weight:730.852
Hs Code.:

Synonyms:(4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

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Chemical Property of (4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

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Technology Process of (4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

There total 18 articles about (4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl 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: 83.0%

: (4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-[4-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethoxy-phenyl]-3-oxo-heptanoic acid tert-butyl ester

: 152401-21-3
(4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)74079-2

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 152401-21-3
(4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / (i-Pr)2NEt / 22 h / 25 °C

2: 92 percent / (n-Bu)4NF / 0.5 h / 25 °C

3: 99 percent / Et₃N, DMAP / CH₂Cl₂

4: 89 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / 25 °C

5: PDC / dimethylformamide / 19 h / 25 °C

6: NaOH / methanol; H₂O / 0.5 h / 0 °C

8: 93 percent / imidazole / CH₂Cl₂ / 24 h / 25 °C

9: 1.) LDA / 1.) THF, -78 deg C, 2.) 4 h

10: 83 percent / (n-Bu)4NF / tetrahydrofuran / 0.5 h / 25 °C

With 1H-imidazole; dmap; sodium hydroxide; dipyridinium dichromate; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)74079-2

Reference yield:

: 152401-13-3
(4-bromo-2,6-dimethoxyphenoxy)(tert-butyl)dimethylsilane

: 152401-21-3
(4R,5S,6R)-5-Benzyloxy-4,6-bis-benzyloxymethoxy-7-(4-hydroxy-3,5-dimethoxy-phenyl)-3-oxo-heptanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 16 steps

2: Et₃N

3: 98 percent / LiAlH₄

4: 86 percent / 20percent aq. HNO₃ / 1,2-dimethoxy-ethane / 3.5 h / 50 °C

5: 93 percent / NaBH₃CN, CF₃CO₂H / ethanol; tetrahydrofuran / 25 °C

6: 87 percent / imidazole / dimethylformamide; CH₂Cl₂ / -42 °C

7: 85 percent / (i-Pr)2NEt / 22 h / 25 °C

8: 92 percent / (n-Bu)4NF / 0.5 h / 25 °C

9: 99 percent / Et₃N, DMAP / CH₂Cl₂

10: 89 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / 25 °C

11: PDC / dimethylformamide / 19 h / 25 °C

12: NaOH / methanol; H₂O / 0.5 h / 0 °C

14: 93 percent / imidazole / CH₂Cl₂ / 24 h / 25 °C

15: 1.) LDA / 1.) THF, -78 deg C, 2.) 4 h

16: 83 percent / (n-Bu)4NF / tetrahydrofuran / 0.5 h / 25 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; tetrabutyl ammonium fluoride; nitric acid; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)74079-2