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

Base Information

• Chemical Name: (3aR,4S,6R,7S,7aR)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one
• CAS No.: 226885-99-0
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385

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

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

There total 12 articles about (3aR,4S,6R,7S,7aR)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-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: 99.0%

(3aR,4S,6R,7S,7aR)-7-iodo-4-<(methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226885-97-8) → (3aR,4S,6R,7S,7aR)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226885-99-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;

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) → (3aR,4S,6R,7S,7aR)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226885-99-0)

Guidance literature:

Multi-step reaction with 4 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

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

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

Reference yield:

(4S,6S)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-91-2) → (3aR,4S,6R,7S,7aR)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one (226885-99-0)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.33 h / -78 °C

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

4: 94 percent / I₂ / tetrahydrofuran; H₂O / 6 h / 0 °C

5: 99 percent / azobisisobutyronitrile, tributyltin hydride / toluene / 1 h / Heating

With sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; iodine; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; water; toluene; xylene;

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

upstream raw materials:

(3aR,4S,6R,7S,7aR)-7-iodo-4-<(methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

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

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

(3S,4R,6S)-3-hydroxy-6-<(4-methoxybenzyl)oxy>-4-<(methoxymethyl)oxy>-cyclohexene

Downstream raw materials:

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

(+)-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

(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

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