(E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

Base Information

Chemical Name:(E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one
CAS No.:912352-06-8
Molecular Formula:C₁₉H₂₆O₄
Molecular Weight:318.413
Hs Code.:

Synonyms:(E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

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Chemical Property of (E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

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Technology Process of (E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

There total 16 articles about (E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one 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: 66.0%

: 912351-93-0
(E)-(4R,5R,11R)-4-Benzyloxy-5,11-dihydroxy-dodec-2-enoic acid

: 912352-06-8
(E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; toluene; for 24h; Heating;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-95-2
6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal

: 912352-06-8
(E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 78 percent / t-BuOK / dimethylsulfoxide / 1 h / 0 °C

2: 43 percent / S,S-Jacobsen catalyst / H₂O / 12 h / 20 °C

3: 81 percent / LAH / tetrahydrofuran / 1 h / 0 °C

4: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

5: 85 percent / aq. AcOH / 12 h / 70 °C

6: 90 percent / H₅IO₆ / ethyl acetate; H₂O / 1 h / 0 °C

7: 89 percent / toluene / 2 h / Heating

8: 72 percent / aq. NaOH / methanol / 2 h / 20 °C

9: 66 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 24 h / Heating

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; acetic acid; periodic acid; triethylamine; (S,S)-(salen)manganese; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; 7: Wittig olefination / 9: Yamaguchi macrolactonisation;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-99-6
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

: 912352-06-8
(E)-(5R,6R,12R)-5-Benzyloxy-6-hydroxy-12-methyl-oxacyclododec-3-en-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 43 percent / S,S-Jacobsen catalyst / H₂O / 12 h / 20 °C

2: 81 percent / LAH / tetrahydrofuran / 1 h / 0 °C

3: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

4: 85 percent / aq. AcOH / 12 h / 70 °C

5: 90 percent / H₅IO₆ / ethyl acetate; H₂O / 1 h / 0 °C

6: 89 percent / toluene / 2 h / Heating

7: 72 percent / aq. NaOH / methanol / 2 h / 20 °C

8: 66 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 24 h / Heating

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 2,4,6-trichlorobenzoyl chloride; acetic acid; periodic acid; triethylamine; (S,S)-(salen)manganese; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 6: Wittig olefination / 8: Yamaguchi macrolactonisation;
DOI:10.1016/j.tetlet.2006.07.043