Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester
CAS No.:81987-65-7
Molecular Formula:C₂₆H₃₆O₅S
Molecular Weight:460.635
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

There total 10 articles about Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester 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

: 81987-65-7
Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

Guidance literature:: Multi-step reaction with 10 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

9: 94 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

10: pyridine / 18 h / 0 - 5 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 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

: 81987-65-7
Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

Guidance literature:: Multi-step reaction with 9 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

8: 94 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

9: pyridine / 18 h / 0 - 5 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 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:

: 82041-98-3
methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>cyclopentane-1-ethanol

: 81987-65-7
Toluene-4-sulfonic acid (S)-3-[(1S,2R,3S)-3-benzyloxy-2-((S)-1-hydroxy-ethyl)-2-methyl-cyclopentyl]-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 12 h / 0 - 5 °C

2: dimethylsulfoxide / 2 h / 90 °C

3: 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

4: i-Bu₂AlH₄ / toluene / 1 h / -78 °C

5: NaBH₄ / methanol / 2 h / Ambient temperature

6: 94 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

7: pyridine / 18 h / 0 - 5 °C

With sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide; toluene;
DOI:10.1021/ja00379a029