benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

Base Information

Chemical Name:benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate
CAS No.:144534-84-9
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

Synonyms:benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

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Chemical Property of benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

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Technology Process of benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

There total 10 articles about benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate 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: 87.0%

: 172995-74-3
benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-hydroxyprop-2-yl>tetrahydropyran-2-yl>acetate

: 144534-84-9
benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

Guidance literature:: With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 - 20 ℃; for 1h;
DOI:10.1016/0040-4020(95)00905-1

Reference yield:

: 144606-47-3
(2R,4S,5S,6S)-7-benzyloxy-5-hydroxy-2,4,6-trimethylheptanoic acid δ-lactone

: 144534-84-9
benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h / Ambient temperature

2: 89 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

3: tetrahydrofuran / 1 h / -78 °C

4: 1N aq. H₂SO₄ / tetrahydrofuran / 3 h / Ambient temperature

5: 87 percent / pyridine*SO₃, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 - 20 °C

With 1H-imidazole; sulfuric acid; hydrogen; sulfur trioxide pyridine complex; triethylamine; palladium dihydroxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1016/0040-4020(95)00905-1

Reference yield:

: 90093-98-4
(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

: 144534-84-9
benzyl 2-<(2S,3R,5S,6S)-3,5-dimethyl-2-hydroxy-6-<(2S)-1-oxoprop-2-yl>tetrahydropyran-2-yl>acetate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 17 h

2: 76 percent / 1N aq. H₂SO₄ / dioxane / 3.5 h / 50 °C

3: 92 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

4: 96 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h / Ambient temperature

5: 89 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

6: tetrahydrofuran / 1 h / -78 °C

7: 1N aq. H₂SO₄ / tetrahydrofuran / 3 h / Ambient temperature

8: 87 percent / pyridine*SO₃, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 - 20 °C

With 1H-imidazole; 3 A molecular sieve; sulfuric acid; hydrogen; sulfur trioxide pyridine complex; sodium hydride; triethylamine; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1016/0040-4020(95)00905-1