(1aR)-2,2aβ,6,6aβ-Tetrahydro-6α-hydroxy-1a-methyl-5-(4-methyl-3-pentenyl)oxireno[f]benzofuran-4(1aH)-one

Base Information

• Chemical Name: (1aR)-2,2aβ,6,6aβ-Tetrahydro-6α-hydroxy-1a-methyl-5-(4-methyl-3-pentenyl)oxireno[f]benzofuran-4(1aH)-one
• CAS No.: 21764-32-9
• Molecular Formula: C15H20O4
• Molecular Weight: 264.32
• Mol file: 21764-32-9.mol

Synonyms:

Chemical Property of (1aR)-2,2aβ,6,6aβ-Tetrahydro-6α-hydroxy-1a-methyl-5-(4-methyl-3-pentenyl)oxireno[f]benzofuran-4(1aH)-one

Chemical Property:

• Melting Point: 120-121 °C
• Boiling Point: 457.8±45.0 °C(Predicted)
• PKA: 12.98±0.60(Predicted)
• PSA: 59.06000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 1.87690

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aR)-2,2aβ,6,6aβ-Tetrahydro-6α-hydroxy-1a-methyl-5-(4-methyl-3-pentenyl)oxireno[f]benzofuran-4(1aH)-one

There total 37 articles about (1aR)-2,2aβ,6,6aβ-Tetrahydro-6α-hydroxy-1a-methyl-5-(4-methyl-3-pentenyl)oxireno[f]benzofuran-4(1aH)-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:

(1aS,2S,5aS,6aR)-6a-Methyl-3-(4-methyl-pent-3-enyl)-2-triethylsilanyloxy-1a,5a,6,6a-tetrahydro-2H-1,5-dioxa-cyclopropa[f]inden-4-one (162460-70-0) → (+)-paniculide A (21764-32-9,79815-33-1)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 0 ℃; for 5.5h; Yield given;

DOI:10.1246/bcsj.67.3327

Reference yield:

(3αR,4S,6S,7αS)-tetrahydro-4-(hydroxymethyl)-6-methoxy-4H-furo<3,2-c>pyran-2(3H)-one (62158-33-2) → (+)-paniculide A (21764-32-9,79815-33-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / iodine, Ph₃P, imidazole / toluene / 2 h / 70 °C

2: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 5 h / Heating

3: 38 percent / mercury(II) trifluoroacetate / acetone; H₂O / 13 h / Ambient temperature

4: pyridine, methanesulfonyl chloride / 4.5 h / Ambient temperature

5: 1.) CuI, 3.) Et₃N / 1) diethyl ether, THF, -78 deg C, 1 h; 2) THF, diethyl ether, -78 deg C, 1 h; 3) THF, diethyl ether, -78 deg C, 10 min, 0 deg C, 2 h

6: Pd(AAc)2 / acetonitrile / 72 h / Ambient temperature

7: 1.) CeCl₃*7H₂O, NaBH₄, 2.) NaHCO₃, mCPBA / 1) methanol, 0 deg C, 1.5 h; 2) CH₂Cl₂, 0 deg C, 3.5 h, 5 deg C, 12 h

8: 75 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

9: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 20 min, -40 deg C, 1 h; 2) THF, -78 deg C, 20 min, 5 deg C, 15 h

10: 1.) potassium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 5 min; 2) THF, HMPA, -78 deg C, 1 h

11: aq. H₂O₂, pyridine / CH₂Cl₂ / 0.67 h / Ambient temperature

12: AcOH / tetrahydrofuran; H₂O / 6 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; Pd(AAc)2; dihydrogen peroxide; iodine; mercury(II) trifluoroacetate; potassium hexamethylsilazane; sodium hydrogencarbonate; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4020(99)00096-4

Reference yield:

5-iodo-2-methylpent-2-ene (43161-11-1) → (+)-paniculide A (21764-32-9,79815-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -78 deg C, 20 min, -40 deg C, 1 h; 2) THF, -78 deg C, 20 min, 5 deg C, 15 h

2: 1.) potassium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 5 min; 2) THF, HMPA, -78 deg C, 1 h

3: aq. H₂O₂, pyridine / CH₂Cl₂ / 0.67 h / Ambient temperature

4: AcOH / tetrahydrofuran; H₂O / 6 h / 0 °C

With pyridine; dihydrogen peroxide; potassium hexamethylsilazane; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(99)00096-4

upstream raw materials:

(1aS,2S,5aS,6aR)-6a-Methyl-3-(4-methyl-pent-3-enyl)-2-triethylsilanyloxy-1a,5a,6,6a-tetrahydro-2H-1,5-dioxa-cyclopropa[f]inden-4-one

(3αR,4S,6S,7αS)-tetrahydro-4-(hydroxymethyl)-6-methoxy-4H-furo<3,2-c>pyran-2(3H)-one

5-iodo-2-methylpent-2-ene

(3aS,7aS)-6-methyl-3,3a,7,7a-tetrahydrobenzofuran-2,4-dione

Refernces

• 1、 Yamamoto,Narasaka. "Total synthesis of (+)-paniculide A via a catalytic asymmetric Diels-Alder reaction of a 3-borylpropenoic acid derivative". . p. 3327 - 3333. Retrieved 2007/10/02.