1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

Base Information

Chemical Name:1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol
CAS No.:561063-74-9
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

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Chemical Property of 1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

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Technology Process of 1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

There total 11 articles about 1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-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: 72.0%

: 917-57-7
vinyllithium

: 561063-73-8
1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-propan-2-one

: 561063-74-9
1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

Guidance literature:: In diethyl ether; at -78 ℃;

Reference yield:

: 128355-20-4
(3R,4S)-3-tert-butyloxycarbonylmethyl-4-hydroxy-5-tetrahydropyranyloxypentanoic acid γ-lactone

: 561063-74-9
1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 87 percent / DIBALH / tetrahydrofuran / -78 °C

2.1: 99 percent / (+/-)-CSA / 50 °C

3.1: Et₃N; DMAP / dimethylformamide / 0 - 20 °C

4.1: LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: Et₃N / CH₂Cl₂ / 0 °C

8.1: NaI / acetone / Heating

9.1: BuLi / tetrahydrofuran / -78 - 20 °C

9.2: tetrahydrofuran / -78 - 20 °C

10.1: (+/-)-CSA / methanol; H₂O / 60 °C

11.1: 72 percent / diethyl ether / -78 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

Reference yield:

: 561063-79-4
[(2S,3R)-5-Hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl]-acetic acid tert-butyl ester

: 561063-74-9
1-[(2R,3S)-3-(2-Benzyloxy-ethyl)-5-methoxy-tetrahydro-furan-2-yl]-2-methyl-but-3-en-2-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / (+/-)-CSA / 50 °C

2.1: Et₃N; DMAP / dimethylformamide / 0 - 20 °C

3.1: LiAlH₄ / diethyl ether / 0 - 20 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: TBAF / tetrahydrofuran / 20 °C

6.1: Et₃N / CH₂Cl₂ / 0 °C

7.1: NaI / acetone / Heating

8.1: BuLi / tetrahydrofuran / -78 - 20 °C

8.2: tetrahydrofuran / -78 - 20 °C

9.1: (+/-)-CSA / methanol; H₂O / 60 °C

10.1: 72 percent / diethyl ether / -78 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;