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

Base Information

• Chemical Name: (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline
• CAS No.: 109961-18-4
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (4aR^*,5S^*,6S^*,7S^*,8aR^*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)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: 81.0%

(4aR*,5S*,6S*,7S*,8aS*)-2-benzyl-7-((2'-ethylhexanoyl)oxy)-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline (109961-17-3) → (4aR*,5S*,6S*,7S*,8aR*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline (109961-18-4)

Guidance literature:

toluene-4-sulfonic acid; In methanol; at 85 ℃; for 12h;

DOI:10.1021/ja00299a050

Reference yield: 40.0%

(4aR,5S,6R,7R)-2-Benzyl-7-hydroxy-6-methoxy-1,2,3,4,4a,5,6,7-octahydro-isoquinoline-5-carboxylic acid methyl ester (109961-13-9) → (4aR*,5S*,6S*,7S*,8aR*)-2-benzyl-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline (109961-18-4)

Guidance literature:

With hydrogen;

DOI:10.1021/ja00254a036

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-7-hydroxy-6-methoxy-5-(methoxycarbonyl)perhydroisoquinoline (109961-18-4)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/ja00254a036

upstream raw materials:

(4aR,5S,6R,7R)-2-Benzyl-7-hydroxy-6-methoxy-1,2,3,4,4a,5,6,7-octahydro-isoquinoline-5-carboxylic acid methyl ester

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

(+/-)-3-isoreserpine

(+/-)-reserpine

(+/-)-inside 3-isoreserpine

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