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

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((E)-1-methyl-pent-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:209341-02-6
Molecular Formula:C₂₀H₂₈O₄
Molecular Weight:332.44
Hs Code.:

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

There total 1 articles about (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((E)-1-methyl-pent-1-enyl)-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: 86.0%

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

: 1779-51-7
n-butyl(triphenyl)phosphonium bromide

: 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

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 3h;
DOI:10.1016/S0040-4039(98)00588-7

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:

: 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

: 209341-03-7
(3R,5S,6R,7R)-5-Benzyloxy-3,7-dimethyl-undec-1-en-6-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 50 percent / H₂ / Pd/C / ethyl acetate / 7 h

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

3: IBX / dimethylsulfoxide / 20 h / Ambient temperature

4: NaBH₄ / methanol / 3 h / 0 °C

5: NaH / tetrahydrofuran / Ambient temperature

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

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

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

9: K₂CO₃ / methanol / 1 h / Ambient temperature

10: DIBAL-H / toluene / 0.5 h / -78 °C

11: CSA / 2 h / 0 °C

12: 98 percent / H₂ / Rh-Al₂O₃ / diethyl ether / 0.17 h / 0 - 5 °C

13: H₂SO₄ / acetic acid; H₂O / 10 h / Ambient temperature

14: 78 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 0 °C

With sodium tetrahydroborate; sodium periodate; n-butyllithium; 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; palladium on activated charcoal; rhodium on alumina; In tetrahydrofuran; methanol; diethyl ether; water; acetic acid; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1016/S0040-4039(98)00588-7