(2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

Base Information

Chemical Name:(2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran
CAS No.:114144-80-8
Molecular Formula:C₂₀H₃₂O₃
Molecular Weight:320.472
Hs Code.:

Synonyms:(2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

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Chemical Property of (2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

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Technology Process of (2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

There total 23 articles about (2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran 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:

: 26291-75-8,81114-49-0,109200-09-1,128461-80-3
(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 114144-80-8
(2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

Guidance literature:: Multi-step reaction with 12 steps

1: 1) p-toluenesulfonyl chloride, pyridine; 2) K₂CO₃ / 1) 17 h; 2) MeOH, r.t., 40 min

2: 81 percent / lithium aluminium hydride / diethyl ether / 5 h, 0 deg C, then 1 h r.t.

3: 92 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

4: 100 percent / tetrahydrofuran / 2 h / 18 °C

5: BH₃-THF / tetrahydrofuran / 1 h / 0 - 5 °C

6: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

7: 83 percent / aq. HCl / tetrahydrofuran / 10.5 h / 40 °C

8: 94.4 percent / NaIO₄ / methanol; H₂O / 1 h / 0 °C

9: 1) NaH; 2) K₂CO₃ / 1) THF, -80 deg C, then 8 deg C; 2) MeOH, r.t., 1 h

10: 99.4 percent / diisobutylaluminum hydride / toluene / -80 °C

11: 97 percent / camphorsulfonic acid / 1 h / Ambient temperature

12: H₂, 10percent Pd-C / ethyl acetate / 21 h / Ambient temperature

With pyridine; hydrogenchloride; sodium periodate; palladium on activated charcoal; lithium aluminium tetrahydride; borane-THF; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; p-toluenesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1248/cpb.35.2184

Reference yield:

: 90093-98-4
(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

: 100-44-7
benzyl chloride

: 114144-80-8
(2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

Guidance literature:: With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; Ambient temperature;
DOI:10.1016/S0040-4039(00)61139-5

Reference yield:

: 56982-95-7
(3aR,5S,6R,6aR)-2,2,6-trimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

: 114144-80-8
(2S,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-isopropoxytetrahydropyran

Guidance literature:: Multi-step reaction with 11 steps

1: 81 percent / lithium aluminium hydride / diethyl ether / 5 h, 0 deg C, then 1 h r.t.

2: 92 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

3: 100 percent / tetrahydrofuran / 2 h / 18 °C

4: BH₃-THF / tetrahydrofuran / 1 h / 0 - 5 °C

5: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

6: 83 percent / aq. HCl / tetrahydrofuran / 10.5 h / 40 °C

7: 94.4 percent / NaIO₄ / methanol; H₂O / 1 h / 0 °C

8: 1) NaH; 2) K₂CO₃ / 1) THF, -80 deg C, then 8 deg C; 2) MeOH, r.t., 1 h

9: 99.4 percent / diisobutylaluminum hydride / toluene / -80 °C

10: 97 percent / camphorsulfonic acid / 1 h / Ambient temperature

11: H₂, 10percent Pd-C / ethyl acetate / 21 h / Ambient temperature

With hydrogenchloride; sodium periodate; palladium on activated charcoal; lithium aluminium tetrahydride; borane-THF; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1248/cpb.35.2184