2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Base Information

Chemical Name:2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one
CAS No.:402571-25-9
Molecular Formula:C₄₂H₅₆O₉
Molecular Weight:704.901
Hs Code.:

2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Synonyms:2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

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Chemical Property of 2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

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Technology Process of 2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

There total 12 articles about 2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-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: 55.0%

: (2R,4R,5S,6S,10S,11S,12R)-13-Benzyloxy-11-(diethyl-isopropyl-silanyloxy)-2-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-5-(4-methoxy-benzyloxy)-4,6,8,10,12-pentamethyl-tridecane-3,7,9-trione

: 402571-25-9
2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran;
DOI:10.1021/ol017082w

Reference yield:

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

: 402571-25-9
2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Guidance literature:: Multi-step reaction with 9 steps

1: (c-Hex)2BCl; triethylamine

2: LiBH₄

3: imidazole / dimethylformamide

4: pyridinium p-toluenesulfonate / methanol; CH₂Cl₂

5: Dess-Martin periodinane / CH₂Cl₂

6: 92 percent / Sn(OTf)2; triethylamine / CH₂Cl₂

7: pyridinium p-toluenesulfonate / methanol; CH₂Cl₂

8: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂

9: 55 percent / HF*pyridine; pyridine / tetrahydrofuran

With pyridine; 1H-imidazole; lithium borohydride; tin(II) trifluoromethanesulfonate; oxalyl dichloride; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Dess-Martin oxidation / 8: Swern oxidation;
DOI:10.1021/ol017082w

Reference yield:

: 275355-99-2
2-((2S,3S,4S,5R,6R)-3,7-dihydroxy-5-((4-methoxybenzyl)oxy)-4,6-dimethylheptan-2-yl)-6-ethyl-3,5-dimethyl-4H-pyran-4-one

: 402571-25-9
2-[(1R,3R,4S,5S)-5-[(2R,3S,5S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2-hydroxy-3,5-dimethyl-4-oxo-tetrahydro-pyran-2-yl]-4-(4-methoxy-benzyloxy)-1,3-dimethyl-2-oxo-hexyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂

2: potassium carbonate / methanol

3: Dess-Martin periodinane; pyridine / CH₂Cl₂

4: 92 percent / Sn(OTf)2; triethylamine / CH₂Cl₂

5: pyridinium p-toluenesulfonate / methanol; CH₂Cl₂

6: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂

7: 55 percent / HF*pyridine; pyridine / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; oxalyl dichloride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3: Dess-Martin oxidation / 6: Swern oxidation;
DOI:10.1021/ol017082w