3-Methyl-2-butenoic acid [8-hydroxymethyl-1,5-dimethyl-5-(4-methyl-3-pentenyl)-12-oxabicyclo[9.1.0]dodeca-3,7-dien-2-yl] ester

Base Information

Chemical Name:3-Methyl-2-butenoic acid [8-hydroxymethyl-1,5-dimethyl-5-(4-methyl-3-pentenyl)-12-oxabicyclo[9.1.0]dodeca-3,7-dien-2-yl] ester
CAS No.:72506-14-0
Molecular Formula:C₂₅H₃₈O₄
Molecular Weight:402.574
Hs Code.:
Mol file:72506-14-0.mol

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3-Methyl-2-butenoic acid [8-hydroxymethyl-1,5-dimethyl-5-(4-methyl-3-pentenyl)-12-oxabicyclo[9.1.0]dodeca-3,7-dien-2-yl] ester

Chemical Property:

Purity/Quality:: ≥98% （HPLC） ^*data from raw suppliers

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Technology Process of 3-Methyl-2-butenoic acid [8-hydroxymethyl-1,5-dimethyl-5-(4-methyl-3-pentenyl)-12-oxabicyclo[9.1.0]dodeca-3,7-dien-2-yl] ester

There total 15 articles about 3-Methyl-2-butenoic acid [8-hydroxymethyl-1,5-dimethyl-5-(4-methyl-3-pentenyl)-12-oxabicyclo[9.1.0]dodeca-3,7-dien-2-yl] ester 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: 91.0%

: (1E,4S,5E,7R,8R,9R)-8,9-epoxy-4,8-dimethyl-7-(3-methylbut-2-enoyloxy)-4-(4-methylpent-3-enyl)-1-[(4-nitrobenzoyloxy)methyl]cycloundeca-1,5-diene

: 72506-14-0
(+)-vibsanin A

Guidance literature:: With sodium methylate; In methanol; at 0 ℃; for 12h; chemoselective reaction; Enzymatic reaction;
DOI:10.1021/acs.orglett.5b00086

Reference yield:

: 5389-87-7
1-chloro-3,7-dimethylocta-2,6-diene

: 72506-14-0
(+)-vibsanin A

Guidance literature:: Multi-step reaction with 14 steps

1.1: ammonium chloride; zinc / water; tetrahydrofuran / 42 h / -5 °C

1.2: 0.33 h / 0 °C

2.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 19 h / 0 - 20 °C

3.1: Martins sulfurane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

4.1: zinc(II) nitrate hexahydrate / acetonitrile / 24 h / 50 °C

5.1: lithium; ammonia / diethyl ether / 0.33 h / -78 °C

6.1: sodium periodate / methanol; water / 3 h / 0 - 20 °C

7.1: chromium dichloride / 1,4-dioxane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

8.1: tert.-butyl lithium / pentane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

9.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / -15 °C / Inert atmosphere

9.2: 3.5 h / -15 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C / Enzymatic reaction

11.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 °C / Enzymatic reaction

12.1: chromium dichloride; nickel dichloride / dimethyl sulfoxide / 17 h / 30 °C / Inert atmosphere; Enzymatic reaction

13.1: triphenylphosphine; diethylazodicarboxylate / toluene / 1 h / 0 °C / Inert atmosphere; Enzymatic reaction

14.1: sodium methylate / methanol / 12 h / 0 °C / Enzymatic reaction

With chromium dichloride; dmap; sodium periodate; Martins sulfurane; zinc(II) nitrate hexahydrate; tetrabutyl ammonium fluoride; ammonia; tert.-butyl lithium; sodium methylate; lithium; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; zinc; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; pentane; 9.1: |Mitsunobu Displacement / 12.1: |Nozaki-Hiyama-Kishi Reaction / 13.1: |Mitsunobu Displacement;
DOI:10.1021/acs.orglett.5b00086

Reference yield:

: (3RS,6S,7R,8S)-7-benzyloxy-6-(2-hydroxyethyl)-8,9-(isopropylidenedioxy)-2,6-dimethylnonan-3-ol

: 72506-14-0
(+)-vibsanin A

Guidance literature:: Multi-step reaction with 13 steps

1.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 19 h / 0 - 20 °C

2.1: Martins sulfurane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3.1: zinc(II) nitrate hexahydrate / acetonitrile / 24 h / 50 °C

4.1: lithium; ammonia / diethyl ether / 0.33 h / -78 °C

5.1: sodium periodate / methanol; water / 3 h / 0 - 20 °C

6.1: chromium dichloride / 1,4-dioxane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

7.1: tert.-butyl lithium / pentane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / -15 °C / Inert atmosphere

8.2: 3.5 h / -15 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C / Enzymatic reaction

10.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 °C / Enzymatic reaction

11.1: chromium dichloride; nickel dichloride / dimethyl sulfoxide / 17 h / 30 °C / Inert atmosphere; Enzymatic reaction

12.1: triphenylphosphine; diethylazodicarboxylate / toluene / 1 h / 0 °C / Inert atmosphere; Enzymatic reaction

13.1: sodium methylate / methanol / 12 h / 0 °C / Enzymatic reaction

With chromium dichloride; dmap; sodium periodate; Martins sulfurane; zinc(II) nitrate hexahydrate; tetrabutyl ammonium fluoride; ammonia; tert.-butyl lithium; sodium methylate; lithium; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; pentane; 8.1: |Mitsunobu Displacement / 11.1: |Nozaki-Hiyama-Kishi Reaction / 12.1: |Mitsunobu Displacement;
DOI:10.1021/acs.orglett.5b00086