(+/-)-Prestegane B

Base Information

• Chemical Name: (+/-)-Prestegane B
• CAS No.: 112019-26-8
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391
• Mol file: 112019-26-8.mol

Synonyms:

Chemical Property of (+/-)-Prestegane B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-Prestegane B

There total 9 articles about (+/-)-Prestegane B 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: 83.0%

(3R*,4R*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone (111959-15-0) → (+/-)-Prestegane B (93376-04-6,112019-26-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; ethyl acetate; under 2585.7 Torr; Ambient temperature; overnight;

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

Reference yield:

4-methoxy-3-(benzyloxy)benzyl bromide (55667-12-4) + 4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone (111959-12-7) → (+/-)-Prestegane B (93376-04-6,112019-26-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -80 ℃;

DOI:10.1021/jo00236a056

Reference yield:

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → (+/-)-Prestegane B (93376-04-6,112019-26-8)

Guidance literature:

Multi-step reaction with 6 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

6: 83 percent / H₂ / 10percent Pd/C / acetic acid; ethyl acetate / 2585.7 Torr / Ambient temperature; overnight

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

upstream raw materials:

4-methoxy-3-(benzyloxy)benzyl bromide

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

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

3-benzyloxy-4-methoxy-benzyl alcohol

Downstream raw materials:

(3R^*,4R^*)-3-(3-hydroxybenzyl)-4-(3-hydroxybenzyl)-4,5-dihydro-2(3H)-furanone <(+/-)-HPMF>

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