2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-ol

Base Information

• Chemical Name: 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-ol
• CAS No.: 742101-65-1
• Molecular Formula: C₃₁H₃₄O₇
• Molecular Weight: 518.607

Synonyms:2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-ol

Chemical Property of 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-ol

Chemical Property:

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Technology Process of 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-ol

There total 7 articles about 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-ol 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%

2-benzyloxy-8,8-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (514826-88-1) + 2-[2-(1-bromo-vinyl)-3-methoxy-5-methyl-phenyl]-[1,3]dioxane (742101-64-0) → 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-ol (742101-65-1)

Guidance literature:

2-[2-(1-bromo-vinyl)-3-methoxy-5-methyl-phenyl]-[1,3]dioxane; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.166667h;

2-benzyloxy-8,8-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

DOI:10.1021/ol049261u

Reference yield:

methyl-3-methoxy-5-methyl-2-(trifluoromethanesulfonyloxy)benzoate (175165-88-5) → 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-ol (742101-65-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 68 percent / (Ph₃P)2PdCl₂; Et₃N / dimethylformamide / 7 h / 90 °C

2.1: 96 percent / K₂CO₃ / methanol / 1 h / 25 °C

3.1: 95 percent / Et₄N⁽¹⁺⁾*(HBr₂)^(1-) / CH₂Cl₂ / 0.5 h / 25 °C

4.1: 90 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -78 - 0 °C

5.1: 89 percent / MnO₂ / CHCl₃ / 7.5 h / Heating

6.1: 85 percent / TsOH / toluene / 0.75 h / Heating

7.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C

7.2: 100 percent / tetrahydrofuran / 0.08 h / -78 °C

With manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; Et₄N⁽¹⁺⁾*(HBr₂)^(1-); tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1.1: Sonogashira reaction;

DOI:10.1021/ol049261u

Reference yield:

2-(1-bromo-vinyl)-3-methoxy-5-methyl-benzaldehyde (742101-69-5) → 2-benzyloxy-7-[1-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-vinyl]-8,8-dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-ol (742101-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / TsOH / toluene / 0.75 h / Heating

2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C

2.2: 100 percent / tetrahydrofuran / 0.08 h / -78 °C

With tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

DOI:10.1021/ol049261u

upstream raw materials:

2-benzyloxy-8,8-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one

2-[2-(1-bromo-vinyl)-3-methoxy-5-methyl-phenyl]-[1,3]dioxane

methyl-3-methoxy-5-methyl-2-(trifluoromethanesulfonyloxy)benzoate

2-(1-bromo-vinyl)-3-methoxy-5-methyl-benzaldehyde

Downstream raw materials:

1-benzyloxy-10,12-dimethoxy-8-methyl-6H-benzo[d]naphtho[1,2-b]pyran-6-one

acetic acid 5-benzyloxy-2-(2-formyl-6-methoxy-4-methyl-phenyl)-4-methoxy-naphthalen-1-yl ester

acetic acid 5-benzyloxy-2-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-4-methoxy-naphthalen-1-yl ester

5-benzyloxy-2-(2-[1,3]dioxan-2-yl-6-methoxy-4-methyl-phenyl)-4-methoxy-naphthalen-1-ol

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