(4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline

Base Information

• Chemical Name: (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline
• CAS No.: 96648-96-3
• Molecular Formula: C₂₉H₃₇NO₈
• Molecular Weight: 527.615

Synonyms:(4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline

Chemical Property of (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline

Chemical Property:

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Technology Process of (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline

There total 15 articles about (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline 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: 91.0%

3,4,5-Trimethoxybenzoyl chloride (4521-61-3) + (4aR*,5S*,6S*,7S*,8aR*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline (109961-18-4) → (4aR*,5S*,6S*,7S*,8aR*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline (96648-96-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00299a050

Reference yield:

(4aR*,5S*,6S*,7R*)-2-benzyl-3,4,4a,5,6,7-hexahydro-5-((methoxymethoxy)methyl)-6,7-oxy-1(2H)-isoquinolone (96648-91-8) → (4aR*,5S*,6S*,7S*,8aR*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline (96648-96-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / lithium 2-ethylhexanoate / 1,2-dimethoxy-ethane / 16 h / Heating

2: 98 percent / Ag₂O, CaSO₄ / 96 h / Ambient temperature

3: acid / methanol

4: pyridinium dichromate / dimethylformamide

6: alane

7: methanol / acid

8: 40 percent / hydrogen

9: 91 percent / 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 24 h / Ambient temperature

With methanol; dmap; calcium sulfate; dipyridinium dichromate; hydrogen; aluminium hydride; lithium 2-ethylhexanoate; silver(l) oxide; acid; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00254a036

Reference yield:

(4aR*,5S*,6S*,7S*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-3,4,4a,5,6,7-hexahydro-6-hydroxy-5-((methoxymethoxy)methyl)-1(2H)-isoquinolone (96648-92-9) → (4aR*,5S*,6S*,7S*,8aR*)-2-benzyl-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline (96648-96-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / Ag₂O, CaSO₄ / 96 h / Ambient temperature

2: acid / methanol

3: pyridinium dichromate / dimethylformamide

5: alane

6: methanol / acid

7: 40 percent / hydrogen

8: 91 percent / 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 24 h / Ambient temperature

With methanol; dmap; calcium sulfate; dipyridinium dichromate; hydrogen; aluminium hydride; silver(l) oxide; acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00254a036

upstream raw materials:

3,4,5-Trimethoxybenzoyl chloride

(4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline

(4aR^*,5S^*,6S^*,7R^*)-2-benzyl-3,4,4a,5,6,7-hexahydro-5-((methoxymethoxy)methyl)-6,7-oxy-1(2H)-isoquinolone

(4aR^*,5S^*,6S^*,7S^*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-3,4,4a,5,6,7-hexahydro-6-hydroxy-5-((methoxymethoxy)methyl)-1(2H)-isoquinolone

Downstream raw materials:

(4aR^*,5S^*,6S^*,7S^*,8aR^*)-6-methoxy-5-(methoxycarbonyl)-7-((3,4,5-trimethoxybenzoyl)oxy)perhydroisoquinoline

(+/-)-3-isoreserpine

(+/-)-reserpine

(+/-)-inside 3-isoreserpine

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