(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

Base Information

Chemical Name:(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol
CAS No.:96823-48-2
Molecular Formula:C₃₀H₄₂O₅
Molecular Weight:482.66
Hs Code.:

Synonyms:(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

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Chemical Property of (2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

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Technology Process of (2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

There total 11 articles about (2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-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: 86.0%

: 27150-99-8
1,1-dimethoxy-1-(4-methoxyphenyl)ethane

: 96823-40-4
(2S,3R,6R,7S)-3-benzyloxy-3-ethyl-7-methylundec-10-ene-2,6,7-triol

: 96823-48-2
(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

Guidance literature:: With (1S)-10-camphorsulfonic acid; In dichloromethane; Ambient temperature;
DOI:10.1016/S0040-4039(00)98547-2

Reference yield: 86.0%

: 27150-99-8
1,1-dimethoxy-1-(4-methoxyphenyl)ethane

: 96823-48-2
(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1248/cpb.37.1705

Reference yield:

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

: 96823-48-2
(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

Guidance literature:: Multi-step reaction with 10 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

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