(2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

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Chemical Name:(2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran
CAS No.:116216-85-4
Molecular Formula:C₂₇H₄₀O₆
Molecular Weight:460.611
Hs Code.:

Synonyms:(2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

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Chemical Property of (2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

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Technology Process of (2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

There total 20 articles about (2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>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: 88.0%

: 116216-84-3
(2R,4aR,6R,8aS)-2-<(S)-2-(Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

: 116216-85-4
(2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

Guidance literature:: With hydrogenchloride; In methanol; for 2h; Ambient temperature;
DOI:10.1021/jo00304a022

Reference yield:

: 116428-25-2,121468-42-6,121468-43-7
(E)-(6S,7R)-14-Benzyloxy-6-methoxymethoxy-2,6,10-trimethyl-9-phenylsulfanyl-tetradeca-2,10-dien-7-ol

: 116216-85-4
(2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

Guidance literature:: Multi-step reaction with 12 steps

1: 77 percent / Na / tetrahydrofuran; propan-2-ol / 3 h / Heating

2: 72 percent / t-BuOOH / VO(acac)2 / CH₂Cl₂ / 7 h / Ambient temperature

3: 1.) MsCl, Et₃N, 2.) Ag₂CO₃ / 1.) CH₂Cl₂, rt, 12 h, 2.) aq acetone, 50 deg C

4: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / 0 °C

5: 82 percent / Li, NH₃ / tetrahydrofuran / 1 h / -78 °C

6: 1.) PDC, NaOAc / 1.) CH₂Cl₂, rt, 30 min, 2.) CH₂Cl₂, heating, 3 h

7: 92 percent / DIBAH / hexane / 0.17 h / -78 °C

8: t-BuOOH, Ti(Oi-Pr)4, L-(+)-DIPT / CH₂Cl₂ / 4 h / -20 °C

9: n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

10: 49 percent / Ti(Oi-Pr)4 / toluene / 12 h / Heating

11: 79 percent / Et₃N / CH₂Cl₂

12: 82 percent / HCl / methanol / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; dipyridinium dichromate; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; ammonia; sodium acetate; sodium; lithium; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; silver carbonate; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; hexane; dichloromethane; isopropyl alcohol; toluene;
DOI:10.1016/S0040-4039(00)96808-4

Reference yield:

: 109307-91-7
2-methyl-6-(phenylmethoxy)-2(E)-hexen-1-ol

: 116216-85-4
(2R,4aR,6R,8aS)-2-<(S)-2-Benzoyloxy)-1-hydroxy-1-methylethyl>octahydro-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

Guidance literature:: Multi-step reaction with 15 steps

1: 76 percent / CCl₄, PPh₃ / benzene / Heating

2: 93 percent / dimethylformamide / 0 °C

3: 78 percent / n-BuLi, DABCO / tetrahydrofuran / 3 h / -78 °C

4: 77 percent / Na / tetrahydrofuran; propan-2-ol / 3 h / Heating

5: 72 percent / t-BuOOH / VO(acac)2 / CH₂Cl₂ / 7 h / Ambient temperature

6: 1.) MsCl, Et₃N, 2.) Ag₂CO₃ / 1.) CH₂Cl₂, rt, 12 h, 2.) aq acetone, 50 deg C

7: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / 0 °C

8: 82 percent / Li, NH₃ / tetrahydrofuran / 1 h / -78 °C

9: 1.) PDC, NaOAc / 1.) CH₂Cl₂, rt, 30 min, 2.) CH₂Cl₂, heating, 3 h

10: 92 percent / DIBAH / hexane / 0.17 h / -78 °C

11: t-BuOOH, Ti(Oi-Pr)4, L-(+)-DIPT / CH₂Cl₂ / 4 h / -20 °C

12: n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

13: 49 percent / Ti(Oi-Pr)4 / toluene / 12 h / Heating

14: 79 percent / Et₃N / CH₂Cl₂

15: 82 percent / HCl / methanol / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; tetrachloromethane; dmap; dipyridinium dichromate; n-butyllithium; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; ammonia; sodium acetate; sodium; lithium; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; triphenylphosphine; silver carbonate; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; benzene;
DOI:10.1016/S0040-4039(00)96808-4