(4aR^*,5S^*,6S^*,7S^*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Base Information

• Chemical Name: (4aR^*,5S^*,6S^*,7S^*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline
• CAS No.: 102673-35-8
• Molecular Formula: C₃₃H₄₃NO₅
• Molecular Weight: 533.708

Synonyms:(4aR^*,5S^*,6S^*,7S^*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Chemical Property of (4aR^*,5S^*,6S^*,7S^*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR^*,5S^*,6S^*,7S^*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline

There total 9 articles about (4aR^*,5S^*,6S^*,7S^*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline 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: 89.0%

(4aR*,5S*,6S*,7S*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-3,4,4a,5,6,7-hexahydro-5-(methoxycarbonyl)-1(2H)-isoquinolone (102673-36-9) → (4aR*,5S*,6S*,7S*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline (102673-35-8)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; at -70 - -25 ℃; for 2h;

DOI:10.1016/S0040-4039(00)95001-9

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*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline (102673-35-8)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 76 percent / Ag₂O, CaSO₄ / 84 h / 50 °C

3: 86 percent / p-toluenesulfonic acid / methanol / 30 h / 40 °C

4: 84 percent / pyridinium dichromate / dimethylformamide / 20 h / 25 °C

5: 96 percent / diethyl ether; methanol / 0.25 h / 0 °C

6: 89 percent / 0.25 M alane / tetrahydrofuran / -78 to -20 deg C, 1.5 h, then -20 to -30 deg C, 0.5 h

With calcium sulfate; dipyridinium dichromate; aluminium hydride; lithium 2-ethylhexanoate; toluene-4-sulfonic acid; silver(l) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; 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*)-2-benzyl-6-(benzyloxy)-7-((2'-ethylhexanoyl)oxy)-5-(methoxycarbonyl)-1,2,3,4,4a,5,6,7-octahydroisoquinoline (102673-35-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / Ag₂O, CaSO₄ / 84 h / 50 °C

2: 86 percent / p-toluenesulfonic acid / methanol / 30 h / 40 °C

3: 84 percent / pyridinium dichromate / dimethylformamide / 20 h / 25 °C

4: 96 percent / diethyl ether; methanol / 0.25 h / 0 °C

5: 89 percent / 0.25 M alane / tetrahydrofuran / -78 to -20 deg C, 1.5 h, then -20 to -30 deg C, 0.5 h

With calcium sulfate; dipyridinium dichromate; aluminium hydride; toluene-4-sulfonic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja00254a036

upstream raw materials:

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

(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

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

Downstream raw materials:

(+/-)-19,20-dehydro-α-yohimbine

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

(4aS,5R,6R)-6-Acetoxy-2-benzyl-1,2,3,4,4a,5,6,7-octahydro-isoquinoline-5-carboxylic acid methyl ester

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