(2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

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Chemical Name:(2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one
CAS No.:146517-47-7
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:(2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

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Chemical Property of (2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

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Technology Process of (2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

There total 8 articles about (2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one 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:

: 116652-75-6
(R)-1-(benzyloxy)-2-methylpentan-3-one

: 146517-47-7
(2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / Sn(OTf)2, Et₃N / CH₂Cl₂ / -78 °C

2: 87 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -23 °C

3: 2,6-lutidine / CH₂Cl₂ / 20 °C

4: H₂ / 10percent Pd/C / ethanol / 20 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to -41 deg C

6: 1.) (c-C₆H₁₁)2BCl, Et₃N, 2.) H₂O₂, pH 7 buffer / 1.) Et₂O, from -78 deg C to -5 deg C, 2.) MeOH

7: 72 percent / HF, pyridine / tetrahydrofuran / 20 °C

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to -41 deg C

With pyridine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; oxalyl dichloride; pH 7 buffer; dicyclohexylboron chloride; hydrogen fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/ja00057a074

Reference yield:

: 143627-34-3
(2R,4S,5R)-1-Benzyloxy-5-hydroxy-2,4-dimethyl-heptan-3-one

: 146517-47-7
(2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -23 °C

2: 2,6-lutidine / CH₂Cl₂ / 20 °C

3: H₂ / 10percent Pd/C / ethanol / 20 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to -41 deg C

5: 1.) (c-C₆H₁₁)2BCl, Et₃N, 2.) H₂O₂, pH 7 buffer / 1.) Et₂O, from -78 deg C to -5 deg C, 2.) MeOH

6: 72 percent / HF, pyridine / tetrahydrofuran / 20 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to -41 deg C

With pyridine; 2,6-dimethylpyridine; oxalyl dichloride; pH 7 buffer; dicyclohexylboron chloride; hydrogen fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/ja00057a074

Reference yield:

: (4R,5S,6R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinane

: 146517-47-7
(2R,3R,5S,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-6-((R)-1-methyl-2-oxo-butyl)-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / 10percent Pd/C / ethanol / 20 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to -41 deg C

3: 1.) (c-C₆H₁₁)2BCl, Et₃N, 2.) H₂O₂, pH 7 buffer / 1.) Et₂O, from -78 deg C to -5 deg C, 2.) MeOH

4: 72 percent / HF, pyridine / tetrahydrofuran / 20 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to -41 deg C

With pyridine; oxalyl dichloride; pH 7 buffer; dicyclohexylboron chloride; hydrogen fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol;
DOI:10.1021/ja00057a074