(5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

Base Information

• Chemical Name: (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one
• CAS No.: 213692-64-9
• Molecular Formula: C₂₆H₂₇N₃O₆S
• Molecular Weight: 509.583

Synonyms:(5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

Chemical Property of (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

Chemical Property:

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Technology Process of (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

There total 9 articles about (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 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: 68.0%

4-bromo-1-methyl-1H-imidazole-5-carbaldehyde (141524-74-5) + (5R,10aR)-9-mercapto-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one (213692-63-8) → (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one (213692-64-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

DOI:10.1016/S0040-4039(98)01232-5

Reference yield:

1-(chloromethyl)-3,5-dimethoxy-2-{[(4-methoxyphenyl)methyl]thio}benzene (174905-86-3) → (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one (213692-64-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) diisopropylamine, BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) THF, hexane, -78 deg C, 2 h, -50 deg C, 18 h

2: aq. HCl / methanol

3: 96 percent

4: 1.) hexamethyldisiloxane, P₂O₅, 2.) NaBH₄ / 1) CHCl₃, reflux, 10 h; 2) MeOH, -78 deg C, 1 h

5: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

6: 98 percent / NaOEt / ethanol / 20 h / Heating

7: 1.) mercuric trifluoroacetate, anisole, 2.) NaBH₄ / 1) EtOH, rt, 16-19 h; 2) EtOH, 0 deg C, 15 min

8: 68 percent / NaH / dimethylformamide / 3.25 h / 100 °C

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; Hexamethyldisiloxane; sodium ethanolate; mercury(II) trifluoroacetate; phosphorus pentoxide; sodium hydride; methoxybenzene; diisopropylamine; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(99)00199-4

Reference yield:

N-<(4-methoxxyphenyl)acetyl>-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester (213692-59-2) → (5R,10aR)-9-<(5-formyl-1-methyl-1H-imidazol-4-yl)thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one (213692-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) hexamethyldisiloxane, P₂O₅, 2.) NaBH₄ / 1) CHCl₃, reflux, 10 h; 2) MeOH, -78 deg C, 1 h

2: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

3: 98 percent / NaOEt / ethanol / 20 h / Heating

4: 1.) mercuric trifluoroacetate, anisole, 2.) NaBH₄ / 1) EtOH, rt, 16-19 h; 2) EtOH, 0 deg C, 15 min

5: 68 percent / NaH / dimethylformamide / 3.25 h / 100 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; Hexamethyldisiloxane; sodium ethanolate; mercury(II) trifluoroacetate; phosphorus pentoxide; sodium hydride; methoxybenzene; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(99)00199-4

upstream raw materials:

4-bromo-1-methyl-1H-imidazole-5-carbaldehyde

(5R,10aR)-9-mercapto-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

1-(chloromethyl)-3,5-dimethoxy-2-{[(4-methoxyphenyl)methyl]thio}benzene

3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester

Downstream raw materials:

(1R,3R)-5-<<3-hydroxymethyl-6,8-dimethoxy-1-<(4-methoxyphenyl)methyl>-1,2,3,4-tetrahydroisoquinolin-5-yl>thio>-3-methyl-L-histidine methyl ester

(1R,3R)-5-<<6,8-dimethoxy-3-(methoxycarbonyl)-1-<(4-methoxyphenyl)methyl>-1,2,3,4-tetrahydroisoquinolin-5-yl>thio>-3-methyl-L-histidine methyl ester

(5R,10aR)-5-<<6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-3(3H)-oxo-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-9-yl>thio>-3-methyl-L-histidine methyl ester

(5R,10aR)-9-<<5-<<(2R-trans)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazin-5-yl>methyl>-1-methyl-1H-imidazol-4-yl>thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

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