(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:209340-85-2
Molecular Formula:C₂₀H₃₀O₄
Molecular Weight:334.456
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

There total 2 articles about (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole 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: 45.0%

: 209341-02-6
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((E)-1-methyl-pent-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole

: 209340-85-2
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

: (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((S)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 7h;
DOI:10.1016/S0040-4039(98)00588-7

Reference yield:

: 41670-98-8
3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranos-5-ulose

: 209340-85-2
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / n-BuLi / tetrahydrofuran / 3 h / -78 - 0 °C

2: 50 percent / H₂ / Pd/C / ethyl acetate / 7 h

With n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;
DOI:10.1016/S0040-4039(98)00588-7

Reference yield:

: 209340-85-2
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-1-methyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

: 209340-90-9
(2R,3S,5R,6S)-3-Benzyloxy-6-isopropoxy-5-methyl-2-((R)-1-methyl-pentyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 11 steps

1: Ca/liq.NH₃ / diethyl ether / 1 h / -78 °C

2: IBX / dimethylsulfoxide / 20 h / Ambient temperature

3: NaBH₄ / methanol / 3 h / 0 °C

4: NaH / tetrahydrofuran / Ambient temperature

5: H₂SO₄ / acetic acid; H₂O / 12 h / Ambient temperature

6: NaIO₄ / methanol; H₂O / 3 h / Ambient temperature

7: NaH / tetrahydrofuran / 5 h / -78 °C

8: K₂CO₃ / methanol / 1 h / Ambient temperature

9: DIBAL-H / toluene / 0.5 h / -78 °C

10: CSA / 2 h / 0 °C

11: 98 percent / H₂ / Rh-Al₂O₃ / diethyl ether / 0.17 h / 0 - 5 °C

With sodium tetrahydroborate; sodium periodate; sulfuric acid; camphor-10-sulfonic acid; ammonia; hydrogen; sodium hydride; diisobutylaluminium hydride; calcium; potassium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; rhodium on alumina; In tetrahydrofuran; methanol; diethyl ether; water; acetic acid; dimethyl sulfoxide; toluene;
DOI:10.1016/S0040-4039(98)00588-7