(3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

Base Information

• Chemical Name: (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one
• CAS No.: 226886-02-8
• Molecular Formula: C₂₃H₃₂O₇S
• Molecular Weight: 452.569
• Mol file: 226886-02-8.mol

Synonyms:(3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

Chemical Property of (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

There total 16 articles about (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-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: 100.0%

methanesulfonyl chloride (124-63-0) + (3S,3aR,4S,6R,7aS)-6-hydroxy-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226886-01-7) → (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226886-02-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

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

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226886-02-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, 0 deg C, 3 h

2: 89 percent / acetic acid / H₂O / 1.5 h / 70 °C

3: 1.27 g / Ph₃P, imidazole, iodine / toluene / 24 h / Ambient temperature

4: 82 percent / diisopropylethylamine / CH₂Cl₂ / 96 h / Ambient temperature

5: 85 percent / potassium t-butoxide / tetrahydrofuran / 3.5 h / Ambient temperature

6: mercury(II) trifluoroacetate / H₂O / 24 h / Ambient temperature

7: MsCl, Et₃N / CH₂Cl₂ / 6 h / Ambient temperature

8: 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 24 h / Ambient temperature

9: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.33 h / -78 °C

10: 89 percent / molecular sieves 3 Angstroem / xylene / 24 h / 140 °C

11: 94 percent / I₂ / tetrahydrofuran; H₂O / 6 h / 0 °C

12: 99 percent / azobisisobutyronitrile, tributyltin hydride / toluene / 1 h / Heating

13: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -20 deg C, 15 min; 2) THF, -20 deg C, 30 min, 5 deg C, 2 h

14: 93 percent / acetyl chloride / methanol / 96 h / 0 °C

15: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; potassium tert-butylate; iodine; tri-n-butyl-tin hydride; mercury(II) trifluoroacetate; sodium hydride; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; toluene; xylene;

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

Reference yield:

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-92-3) → (3S,3aR,4S,6R,7aS)-6-<(methanesulfonyl)oxy>-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226886-02-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.33 h / -78 °C

2: 89 percent / molecular sieves 3 Angstroem / xylene / 24 h / 140 °C

3: 94 percent / I₂ / tetrahydrofuran; H₂O / 6 h / 0 °C

4: 99 percent / azobisisobutyronitrile, tributyltin hydride / toluene / 1 h / Heating

5: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -20 deg C, 15 min; 2) THF, -20 deg C, 30 min, 5 deg C, 2 h

6: 93 percent / acetyl chloride / methanol / 96 h / 0 °C

7: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; iodine; tri-n-butyl-tin hydride; triethylamine; acetyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; toluene; xylene;

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

upstream raw materials:

methanesulfonyl chloride

(3S,3aR,4S,6R,7aS)-6-hydroxy-4-<(4-methoxybenzyl)oxy>-3-(4-methyl-3-pentenyl)-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

p-methoxybenzyl chloride

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one

Downstream raw materials:

(+)-paniculide A

(1aR,2aS,5S,5aS,6S,6aS)-2,2a,5,5a,6,6a-hexahydro-1a-methyl-5-(4-methyl-3-pentenyl)-5-phenylseleno-6-<(triethylsilyl)oxy>oxirenobenzofuran-4(1aH)-one