(3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone

Base Information

• Chemical Name: (3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone
• CAS No.: 111959-15-0
• Molecular Formula: C₃₄H₃₄O₆
• Molecular Weight: 538.64

Synonyms:(3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone

Chemical Property of (3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone

There total 7 articles about (3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone 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:

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → (3R*,4R*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone (111959-15-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / NaOMe / methanol / 2 h / Heating

2: 1.) KOH; 2.) CaCl₂, NaBH₄ / 1.) EtOH, r.t.; 2.) aq. KOH, r.t., 3 h

3: 84 percent / H₂ / 10percent Pd/C / acetic acid; ethyl acetate / 2585.7 Torr / Ambient temperature; overnight

4: 96 percent / K₂CO₃ / NaI / acetone / 10 h / Heating

5: 1.) n-BuLi, hexamethyldisilazane; 2.) hexamethylphosphoramide / 1.) THF, a) -78 deg C, 1 h, b) -30 deg C, 20 min; 2.) -78 deg C to r.t., 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; sodium methylate; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; calcium chloride; palladium on activated charcoal; sodium iodide; In methanol; acetic acid; ethyl acetate; acetone;

DOI:10.1016/S0040-4020(01)88186-2

Reference yield:

benzyl chloride (100-44-7) → (3R*,4R*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone (111959-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / K₂CO₃ / NaI / acetone / 10 h / Heating

2: 1.) n-BuLi, hexamethyldisilazane; 2.) hexamethylphosphoramide / 1.) THF, a) -78 deg C, 1 h, b) -30 deg C, 20 min; 2.) -78 deg C to r.t., 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; In acetone;

DOI:10.1016/S0040-4020(01)88186-2

Reference yield:

4-(3-hydroxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone (140161-07-5) → (3R*,4R*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone (111959-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / K₂CO₃ / NaI / acetone / 10 h / Heating

2: 1.) n-BuLi, hexamethyldisilazane; 2.) hexamethylphosphoramide / 1.) THF, a) -78 deg C, 1 h, b) -30 deg C, 20 min; 2.) -78 deg C to r.t., 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; In acetone;

DOI:10.1016/S0040-4020(01)88186-2

upstream raw materials:

4-methoxy-3-(benzyloxy)benzyl bromide

4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone

3-benzyloxy-4-methoxy-benzyl alcohol

benzyl chloride

Downstream raw materials:

(M^*,3aR^*,13aR^*)-3a,4,13,13a-tetrahydro-6,11-dibenzoxy-7,10-dimethoxydibenzo-<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one

(+/-)-Prestegane B

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