3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

Base Information

Chemical Name:3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester
CAS No.:178964-23-3
Molecular Formula:C₃₀H₄₀O₉
Molecular Weight:544.642
Hs Code.:

Synonyms:3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

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Chemical Property of 3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

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Technology Process of 3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

There total 7 articles about 3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl 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: 82.0%

: 100-39-0
benzyl bromide

: 178964-22-2
3-{2-Hydroxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

: 178964-23-3
3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

Guidance literature:: With 18-crown-6 ether; caesium carbonate; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1016/0040-4039(96)00713-7

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 178964-23-3
3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / imidazole / CH₂Cl₂ / Ambient temperature

2: 90 percent / NaH / toluene; dimethylsulfoxide / from 0 degC to room t.

3: 80 percent / KH / dimethylformamide / Ambient temperature

4: 90 percent / K₂CO₃ / dimethylformamide / 95 °C

5: 1.) Br₂; 2.) Et₄NBr, ground sieves (4 Angstroem) / 1.) CH₂Cl₂, 0 degC; 2.) DMF, room t.

6: 92 percent / H₂ / Pd(C) / ethyl acetate / 760 Torr / Ambient temperature

7: 82 percent / Cs₂CO₃, 18-Crown-6 / dimethylformamide / Ambient temperature

With 1H-imidazole; 18-crown-6 ether; 4 A molecular sieve; tetraethylammonium bromide; hydrogen; bromine; potassium hydride; sodium hydride; potassium carbonate; caesium carbonate; palladium on activated charcoal; In dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0040-4039(96)00713-7

Reference yield:

: 286-20-4
cyclohexane-1,2-epoxide

: 178964-23-3
3-{2-Benzyloxy-5-[(1S,2S)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenyl}-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / K₂CO₃ / dimethylformamide / 95 °C

2: 1.) Br₂; 2.) Et₄NBr, ground sieves (4 Angstroem) / 1.) CH₂Cl₂, 0 degC; 2.) DMF, room t.

3: 92 percent / H₂ / Pd(C) / ethyl acetate / 760 Torr / Ambient temperature

4: 82 percent / Cs₂CO₃, 18-Crown-6 / dimethylformamide / Ambient temperature

With 18-crown-6 ether; 4 A molecular sieve; tetraethylammonium bromide; hydrogen; bromine; potassium carbonate; caesium carbonate; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00713-7