(E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester

Base Information

• Chemical Name: (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester
• CAS No.: 892867-47-9
• Molecular Formula: C₃₁H₄₄O₈
• Molecular Weight: 544.686
• Mol file: 892867-47-9.mol

Synonyms:(E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester

Chemical Property of (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester

There total 14 articles about (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl 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: 75.0%

(3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-ol (892867-46-8) + acetylenedicarboxylic acid diethyl ester (762-21-0) → (Z)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester + (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester (892867-47-9)

Guidance literature:

With potassium hydride; In 1,2-dichloro-ethane; at 75 ℃; for 6h;

DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

(3S,4S,5S)-3,4-Dimethyl-5-trityloxymethyl-dihydro-furan-2-one → (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester (892867-47-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C

1.2: 91 percent / SOCl₂; pyridine / 1 h / 0 °C

2.1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

3.1: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

4.1: DBU / acetonitrile / 20 h / 65 °C

5.1: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

6.1: 77 percent / NaBH₄; NiCl₂*6H₂O / methanol; CH₂Cl₂ / 0.17 h / 0 °C

7.1: Et₂AlCl / CH₂Cl₂ / 0.5 h / -78 - 0 °C

8.1: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

9.1: SmI₂; t-BuOH / tetrahydrofuran / 0.5 h / -78 °C

10.1: PPTS / CH₂Cl₂ / 8 h / 20 °C

11.1: TBAF / tetrahydrofuran / 15 h / 50 °C

12.1: 75 percent / KH / 1,2-dichloro-ethane / 6 h / 75 °C

With aluminum oxide; sodium tetrahydroborate; lithium borohydride; selenium(IV) oxide; samarium diiodide; 18-crown-6 ether; tetrabutyl ammonium fluoride; diethylaluminium chloride; pyridinium p-toluenesulfonate; potassium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; nickel dichloride; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 12.1: Michael addition;

DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one (892867-38-8) → (E)-2-((3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-yloxy)-but-2-enedioic acid diethyl ester (892867-47-9)

Guidance literature:

Multi-step reaction with 11 steps

1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

2: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

3: DBU / acetonitrile / 20 h / 65 °C

4: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

5: 77 percent / NaBH₄; NiCl₂*6H₂O / methanol; CH₂Cl₂ / 0.17 h / 0 °C

6: Et₂AlCl / CH₂Cl₂ / 0.5 h / -78 - 0 °C

7: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

8: SmI₂; t-BuOH / tetrahydrofuran / 0.5 h / -78 °C

9: PPTS / CH₂Cl₂ / 8 h / 20 °C

10: TBAF / tetrahydrofuran / 15 h / 50 °C

11: 75 percent / KH / 1,2-dichloro-ethane / 6 h / 75 °C

With aluminum oxide; sodium tetrahydroborate; lithium borohydride; selenium(IV) oxide; samarium diiodide; 18-crown-6 ether; tetrabutyl ammonium fluoride; diethylaluminium chloride; pyridinium p-toluenesulfonate; potassium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; nickel dichloride; tert-butyl alcohol; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 11: Michael addition;

DOI:10.1016/j.tetlet.2006.03.078

upstream raw materials:

(3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-ol

acetylenedicarboxylic acid diethyl ester

(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

(2R,3S,4S)-2-Cyclohex-1-enyl-2,3-dimethyl-5-trityloxy-pentane-1,4-diol

Downstream raw materials:

(-)-tetrodecamycin