(2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

Base Information

Chemical Name:(2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol
CAS No.:618095-75-3
Molecular Formula:C₁₉H₂₆O₂S
Molecular Weight:318.48
Hs Code.:

Synonyms:(2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

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Chemical Property of (2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

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Technology Process of (2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

There total 13 articles about (2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol 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:

: 82740-87-2
(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate

: 618095-75-3
(2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

Guidance literature:: Multi-step reaction with 12 steps

1: K₂CO₃ / methanol / 1 h / 20 °C

2: 21 g / imidazole / dimethylformamide / 0.5 h / 20 °C

3: Et₃N; Me₃N*HCl / toluene / 1 h / 0 °C

4: LiHBEt₃ / tetrahydrofuran / 2 h / 20 °C

5: 9.0 g / TBAF / tetrahydrofuran / 1 h / 20 °C

6: 89 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.5 h / 20 °C

7: nBuLi; HMPA / tetrahydrofuran / 2.5 h / -40 - 60 °C

8: 7.7 g / PPTS / methanol / 2.5 h / 50 - 60 °C

9: 94 percent / Red-Al / toluene / 5 h / 0 - 20 °C

10: 80 percent / molecular sieves 4 Angstroem; Ti(OPr-i)4; (L)-(+)-diethyl tartrate / tert-butyl hydroperoxide / CH₂Cl₂; toluene / 27 h / -23 °C

11: 95 percent / nBu₃P / pyridine / 0.33 h / 0 °C

12: CH₂Cl₂; hexane / 0.25 h / -30 °C

With 1H-imidazole; titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; pyridinium p-toluenesulfonate; trimethylamine hydrochloride; lithium triethylborohydride; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tert.-butylhydroperoxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol035227o

Reference yield:

: 95791-07-4
(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

: 618095-75-3
(2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

Guidance literature:: Multi-step reaction with 11 steps

1: 21 g / imidazole / dimethylformamide / 0.5 h / 20 °C

2: Et₃N; Me₃N*HCl / toluene / 1 h / 0 °C

3: LiHBEt₃ / tetrahydrofuran / 2 h / 20 °C

4: 9.0 g / TBAF / tetrahydrofuran / 1 h / 20 °C

5: 89 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.5 h / 20 °C

6: nBuLi; HMPA / tetrahydrofuran / 2.5 h / -40 - 60 °C

7: 7.7 g / PPTS / methanol / 2.5 h / 50 - 60 °C

8: 94 percent / Red-Al / toluene / 5 h / 0 - 20 °C

9: 80 percent / molecular sieves 4 Angstroem; Ti(OPr-i)4; (L)-(+)-diethyl tartrate / tert-butyl hydroperoxide / CH₂Cl₂; toluene / 27 h / -23 °C

10: 95 percent / nBu₃P / pyridine / 0.33 h / 0 °C

11: CH₂Cl₂; hexane / 0.25 h / -30 °C

With 1H-imidazole; titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; pyridinium p-toluenesulfonate; trimethylamine hydrochloride; lithium triethylborohydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tert.-butylhydroperoxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol035227o

Reference yield:

: 146495-85-4
(2R,3S,6R)-6-allyl-2-[(tert-butyldimethylsilanyloxy)methyl]-3,6-dihydro-3-hydroxy-2H-pyran

: 618095-75-3
(2S,3R)-1-[(2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl]-4-phenylthio-3-methyl-2-butanol

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N; Me₃N*HCl / toluene / 1 h / 0 °C

2: LiHBEt₃ / tetrahydrofuran / 2 h / 20 °C

3: 9.0 g / TBAF / tetrahydrofuran / 1 h / 20 °C

4: 89 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.5 h / 20 °C

5: nBuLi; HMPA / tetrahydrofuran / 2.5 h / -40 - 60 °C

6: 7.7 g / PPTS / methanol / 2.5 h / 50 - 60 °C

7: 94 percent / Red-Al / toluene / 5 h / 0 - 20 °C

8: 80 percent / molecular sieves 4 Angstroem; Ti(OPr-i)4; (L)-(+)-diethyl tartrate / tert-butyl hydroperoxide / CH₂Cl₂; toluene / 27 h / -23 °C

9: 95 percent / nBu₃P / pyridine / 0.33 h / 0 °C

10: CH₂Cl₂; hexane / 0.25 h / -30 °C

With titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; pyridinium p-toluenesulfonate; trimethylamine hydrochloride; lithium triethylborohydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tert.-butylhydroperoxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol035227o