(5R,10aR)-9-<<5-<<(2R-cis)-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

Base Information

• Chemical Name: (5R,10aR)-9-<<5-<<(2R-cis)-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
• CAS No.: 213692-67-2
• Molecular Formula: C₃₅H₄₃N₅O₇S
• Molecular Weight: 677.822

Synonyms:(5R,10aR)-9-<<5-<<(2R-cis)-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

Chemical Property of (5R,10aR)-9-<<5-<<(2R-cis)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,10aR)-9-<<5-<<(2R-cis)-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

There total 13 articles about (5R,10aR)-9-<<5-<<(2R-cis)-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 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:

1-(chloromethyl)-3,5-dimethoxy-2-{[(4-methoxyphenyl)methyl]thio}benzene (174905-86-3) → (5R,10aR)-9-<<5-<<(2R-cis)-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 (213692-67-2)

Guidance literature:

Multi-step reaction with 10 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

9: 80 percent / NaBH₄ / methanol / 1 h / Ambient temperature

10: 1.) SOCl₂ / 1) rt, 1 h; 2) THF, -78 deg C, 2 h, -50 deg C, 14 h

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; 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-<<(2R-cis)-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 (213692-67-2)

Guidance literature:

Multi-step reaction with 7 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

6: 80 percent / NaBH₄ / methanol / 1 h / Ambient temperature

7: 1.) SOCl₂ / 1) rt, 1 h; 2) THF, -78 deg C, 2 h, -50 deg C, 14 h

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

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

Reference yield:

(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-<<(2R-cis)-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 (213692-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / NaH / dimethylformamide / 3.25 h / 100 °C

2: 80 percent / NaBH₄ / methanol / 1 h / Ambient temperature

3: 1.) SOCl₂ / 1) rt, 1 h; 2) THF, -78 deg C, 2 h, -50 deg C, 14 h

With sodium tetrahydroborate; thionyl chloride; sodium hydride; In methanol; N,N-dimethyl-formamide;

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

upstream raw materials:

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine

C₉H₁₅LiN₂O₂

(5R,10aR)-9-<(5-hydroxymethyl-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

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

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-D-histidine methyl ester

(1R,3R)-N-(tert-butoxycarbonyl)-5-<<2-(tert-butoxycarbonyl)-3-formyl-6,8-dimethoxy-1-<(4-methoxyphenyl)methyl>-1,2,3,4-tetrahydroisoquinolin-5-yl>thio>-3-methyl-D-histidine methyl ester

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

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