1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline

Base Information

• Chemical Name: 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline
• CAS No.: 628723-98-8
• Molecular Formula: C₃₄H₃₉NO₇
• Molecular Weight: 573.686
• Mol file: 628723-98-8.mol

Synonyms:1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline

Chemical Property of 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline

There total 12 articles about 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline 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: 86.0%

cycl-isopropylidene malonate (2033-24-1) + (E,Z)-butenyl benzyl ether (51299-14-0) + (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (627862-69-5) → 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline (628723-98-8)

Guidance literature:

With ethylenediamine diacetic acid; In benzene; at 60 ℃; for 17h; sonication;

DOI:10.1002/anie.200351129

Reference yield:

rac-O-triisopropylsilyl-2-(6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-yl)ethanol (627862-88-8) → 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline (628723-98-8)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaHCO₃ / 3.5 h / Heating

2: 11.6 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.17 h / 25 °C

3: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

4: 86 percent / ethylenediammonium diacetate / benzene / 14 h / 60 °C

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; ethylenediamine diacetic acid; In tetrahydrofuran; dichloromethane; benzene; 3: Dess-Martin oxidation / 4: Knoevenagel/hetero-Diels-Alder reaction;

DOI:10.1002/chem.200306039

Reference yield:

O-triisopropylsilyl-2-(6,7-dimethoxy-3,4-dihydro-isoquinoline-1-yl)ethanol (627862-66-2) → 1-(S)-N-carbobenzyloxy-1-(2-benzoxy-3-ethyl-6-oxo-tetrahydropyran-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-isoquinoline (628723-98-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / triethylamine; 1,2-(R,R)-N-tosyl-1,2-diphenylethylenediamine; formic acid / dichloro(p-cymene)ruthenium(II) / dimethylformamide / 0 - 25 °C

2: 86 percent / ethylenediammonium diacetate / benzene / 17 h / 60 °C / sonication

With formic acid; ethylenediamine diacetic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In N,N-dimethyl-formamide; benzene;

DOI:10.1002/anie.200351129

upstream raw materials:

cycl-isopropylidene malonate

(E,Z)-butenyl benzyl ether

(S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

2-(6,7-dimethoxy-3,4-dihydro-2H-isoquinoline-1-yl)ethanol