(4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone

Base Information

Chemical Name:(4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone
CAS No.:201284-28-8
Molecular Formula:C₂₅H₃₂O₅
Molecular Weight:412.526
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone

Chemical Property:

Purity/Quality:

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Technology Process of (4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone

There total 12 articles about (4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone 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:

: (2R,3R,5S)-2-Benzyloxy-8-bromo-5-hydroxy-3-(4-methoxy-benzyloxy)-4,4-dimethyl-7-oxo-octanal

: 201284-28-8
(4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -78 ℃; Yield given;
DOI:10.1248/cpb.45.2113

Reference yield:

: 201284-14-2
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanol

: 201284-28-8
(4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

2: 1.) NaH / 1.) THF, 2.) THF

3: 93 percent / DIBAL / CH₂Cl₂

4: 86 percent / H₂ / Pd/C / ethyl acetate

5: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

6: tetrahydrofuran

7: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

8: Li(TMS)2 / tetrahydrofuran

9: NBS / tetrahydrofuran

10: 1M aq. HCl / tetrahydrofuran

11: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

12: SmI₂ / tetrahydrofuran / -78 °C

With hydrogenchloride; N-Bromosuccinimide; samarium diiodide; oxalyl dichloride; Li(TMS)2; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1248/cpb.45.2113

Reference yield:

: 163275-31-8
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

: 201284-28-8
(4S,5R)-4-Benzyloxy-3-hydroxy-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) NaH / 1.) THF, 2.) THF

2: 93 percent / DIBAL / CH₂Cl₂

3: 86 percent / H₂ / Pd/C / ethyl acetate

4: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

5: tetrahydrofuran

6: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

7: Li(TMS)2 / tetrahydrofuran

8: NBS / tetrahydrofuran

9: 1M aq. HCl / tetrahydrofuran

10: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

11: SmI₂ / tetrahydrofuran / -78 °C

With hydrogenchloride; N-Bromosuccinimide; samarium diiodide; oxalyl dichloride; Li(TMS)2; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1248/cpb.45.2113