(2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

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Chemical Name:(2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one
CAS No.:133329-86-9
Molecular Formula:C₃₁H₃₄O₅
Molecular Weight:486.608
Hs Code.:

Synonyms:(2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

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Chemical Property of (2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

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Technology Process of (2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

There total 10 articles about (2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-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: 73.0%

: 133329-85-8,133398-53-5
(1R,2S,4R)-2-Methoxy-4-methyl-1-(4-methyl-furan-2-yl)-5-trityloxy-pentan-1-ol

: 133329-86-9
(2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

Guidance literature:: With tert.-butylhydroperoxide; bis(acetylacetonato) oxovanadium(IV); In dichloromethane; at 23 ℃; for 2.5h;
DOI:10.1016/S0040-4039(00)71216-0

Reference yield:

: 62396-80-9
(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

: 133329-86-9
(2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: LDA / tetrahydrofuran / 2 h / -78 °C

2: 69 percent / BH₃-SMe₂ / tetrahydrofuran / 2 h / 23 - 65 °C

3: 82 percent / pyridine / CH₂Cl₂ / 96 h / 23 °C

4: 87 percent / DMEU, NaH / tetrahydrofuran / 24 h / -10 - 23 °C

5: 88 percent / TBAF / tetrahydrofuran / 2 h / 23 °C

6: 83 percent / (COCl)2, DMSO, NEt₃ / CH₂Cl₂ / 1.5 h / -50 °C

7: 1) n-butyllithium, 2) ZnBr₂ / 1) Et₂O, -20 deg C, 2h, 2) Et₂O, -78 deg C to -20 deg C

8: 73 percent / tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂ / 2.5 h / 23 °C

With pyridine; 1,3-dimethyl-2-imidazolidinone; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; zinc dibromide; lithium diisopropyl amide; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)71216-0

Reference yield:

: 78259-59-3
2-Bromo-4-methyl-furan

: 133329-86-9
(2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1) n-butyllithium, 2) ZnBr₂ / 1) Et₂O, -20 deg C, 2h, 2) Et₂O, -78 deg C to -20 deg C

2: 73 percent / tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂ / 2.5 h / 23 °C

With tert.-butylhydroperoxide; n-butyllithium; zinc dibromide; bis(acetylacetonato) oxovanadium(IV); In dichloromethane;
DOI:10.1016/S0040-4039(00)71216-0