4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran

Base Information

• Chemical Name: 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran
• CAS No.: 145653-95-8
• Molecular Formula: C₂₅H₃₁NO₈
• Molecular Weight: 473.523

Synonyms:4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran

Chemical Property of 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran

Chemical Property:

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Technology Process of 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran

There total 5 articles about 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran 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:

4-formyl-7-methoxy-2-methylbenzofuran (130627-28-0) → 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran (145653-95-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / CH₃COONH₄ / acetic acid / 1.5 h / Heating

2: LiAlH₄ / tetrahydrofuran; diethyl ether / 0.83 h / Heating

3: 76 percent / 10percent NaOH / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 98 percent / 4-dimethylaminopyridine / acetonitrile / 67 h / Ambient temperature

5: 1.) OsO₄, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h

With pyridine; dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; ammonium acetate; sodium hydrogensulfite; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; acetonitrile;

DOI:10.1248/cpb.40.1993

Reference yield:

7-methoxy-2-methyl-4-(2-nitrovinyl)benzofuran (145653-89-0) → 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran (145653-95-8)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / tetrahydrofuran; diethyl ether / 0.83 h / Heating

2: 76 percent / 10percent NaOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 98 percent / 4-dimethylaminopyridine / acetonitrile / 67 h / Ambient temperature

4: 1.) OsO₄, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h

With pyridine; dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium hydrogensulfite; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1248/cpb.40.1993

Reference yield:

4-(2-N-carbobenzoxyaminoethyl)-7-methoxy-2-methylbenzofuran (145653-90-3) → 4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dihydroxy-7-methoxy-2-methyl-2,3-dihydrobenzofuran (145653-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 4-dimethylaminopyridine / acetonitrile / 67 h / Ambient temperature

2: 1.) OsO₄, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h

With pyridine; dmap; osmium(VIII) oxide; sodium hydrogensulfite; In acetonitrile;

DOI:10.1248/cpb.40.1993

upstream raw materials:

4-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-7-methoxy-2-methylbenzofuran

4-formyl-7-methoxy-2-methylbenzofuran

7-methoxy-2-methyl-4-(2-nitrovinyl)benzofuran

4-(2-N-carbobenzoxyaminoethyl)-7-methoxy-2-methylbenzofuran

Downstream raw materials:

6-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2,3-dimethoxybenzaldehyde

2-carbobenzoxy-1,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

1,2,3,4-tetrahydro-7,8-dimethoxyisoquinoline

6-(2-N-carbobenzoxy-N-carbo-tert-butoxyaminoethyl)-2-hydroxy-3-methoxybenzaldehyde

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