(2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

Base Information

Chemical Name:(2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol
CAS No.:96823-42-6
Molecular Formula:C₂₁H₃₂O₃
Molecular Weight:332.483
Hs Code.:

Synonyms:(2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

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Chemical Property of (2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

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Technology Process of (2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

There total 19 articles about (2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol 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: 92.0%

: 96823-50-6
(2S,3S)-3-[(3R,4S)-3-Benzyloxy-4-(3,4-dimethoxy-benzyloxy)-3-ethyl-pentyl]-2-but-3-enyl-2-methyl-oxirane

: 96823-42-6
(2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃;
DOI:10.1016/S0040-4039(00)98547-2

Reference yield: 90.0%

: 96823-50-6
(5S,6R,9R,10S)-9-benzyloxy-9-ethyl-10-(3,4-dimethoxybenzyloxy)-5-methyl-5,6-epoxyundec-1-ene

: 96823-42-6
(2S,3R)-3-Benzyloxy-5-((2R,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 0.333333h;
DOI:10.1248/cpb.37.1705

Reference yield:

: 126393-85-9
(2S,6S)-2-benzyloxymethoxy-7-(4-methoxybenzyloxy)-6-methoxyethoxymethoxyhept-3-en-3-one

: 96823-42-6
(2S,3R)-3-Benzyloxy-5-((2S,3S)-3-but-3-enyl-3-methyl-oxiranyl)-3-ethyl-pentan-2-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 93 percent / H₂ / Pd-C / ethyl acetate / Ambient temperature

2: tetrahydrofuran / 1.5 h / -78 °C

3: 99 percent / NaH / tetrahydrofuran; dimethylformamide / 60 °C

4: 76 percent / DDQ / benzene / 2 h / Ambient temperature

5: 90 percent / DMSO, (COCl)2 / CH₂Cl₂ / -60 °C

6: 96 percent / tetrahydrofuran / 0 °C

7: 83 percent / DMSO, (COCl)2 / CH₂Cl₂ / -60 °C

8: 94 percent / tetrahydrofuran / -78 °C

9: 62 percent / 4N HCl / tetrahydrofuran / 50 °C

10: 86 percent / 10-camphorsulfonic acid (CSA) / CH₂Cl₂ / Ambient temperature

11: 97 percent / NaH / dimethylsulfoxide; tetrahydrofuran / Ambient temperature

12: 86 percent / 1N HCl / tetrahydrofuran / 50 °C

13: 1.) MesCl, Et₃N; 2.) K₂CO₃

14: 92 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

With hydrogenchloride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)98547-2