(S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol

Base Information

Chemical Name:(S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol
CAS No.:81987-64-6
Molecular Formula:C₂₄H₃₈O₄
Molecular Weight:390.563
Hs Code.:

Synonyms:(S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol

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Chemical Property of (S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol

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Technology Process of (S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol

There total 8 articles about (S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-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:

: 81987-61-3
(S)-2-{(1R,4R,5R)-4-Hydroxy-5-methyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopent-2-enyl}-propionic acid

: 81987-64-6
(S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

2: H₂ / PtO₂ / ethyl acetate / 2.5 h / Ambient temperature

3: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

4: pyridine / 12 h / 0 - 5 °C

5: dimethylsulfoxide / 2 h / 90 °C

6: 88 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 10 h

7: i-Bu₂AlH₄ / toluene / 1 h / -78 °C

8: NaBH₄ / methanol / 2 h / Ambient temperature

With sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1021/ja00379a029

Reference yield:

: 82041-93-8
methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

: 81987-64-6
(S)-3-{(1S,2R,3S)-3-Benzyloxy-2-methyl-2-[(S)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-butan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: H₂ / PtO₂ / ethyl acetate / 2.5 h / Ambient temperature

2: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

3: pyridine / 12 h / 0 - 5 °C

4: dimethylsulfoxide / 2 h / 90 °C

5: 88 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 10 h

6: i-Bu₂AlH₄ / toluene / 1 h / -78 °C

7: NaBH₄ / methanol / 2 h / Ambient temperature

With sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1021/ja00379a029