(2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

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Chemical Name:(2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran
CAS No.:618095-76-4
Molecular Formula:C₂₀H₂₈O₃S
Molecular Weight:348.507
Hs Code.:

Synonyms:(2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

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Chemical Property of (2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

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Technology Process of (2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

There total 15 articles about (2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran 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: 90.0%

: 618096-05-2
(2S,6R)-6-Allyl-2-((2S,3R)-2-methoxy-3-methyl-4-phenylsulfanyl-butyl)-3,6-dihydro-2H-pyran

: 618095-76-4
(2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

Guidance literature:: With sodium periodate; In methanol; water; at 20 ℃; for 3h;
DOI:10.1021/ol035227o

Reference yield:

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

: 618095-76-4
(2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 14 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

13: 8.6 g / NaH / dimethylformamide / 0.5 h / 50 °C

14: 90 percent / NaIO₄ / methanol; H₂O / 3 h / 20 °C

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

: 618095-76-4
(2S,6R)-6-allyl-2-[(2S,3R)-4-benzenesulfonyl-2-methoxy-3-methyl-butyl]-3,6-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 13 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

12: 8.6 g / NaH / dimethylformamide / 0.5 h / 50 °C

13: 90 percent / NaIO₄ / methanol; H₂O / 3 h / 20 °C

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