(5S,10aS)-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

Base Information

• Chemical Name: (5S,10aS)-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
• CAS No.: 221332-83-8
• Molecular Formula: C₂₉H₃₄N₄O₇S
• Molecular Weight: 582.678
• Mol file: 221332-83-8.mol

Synonyms:(5S,10aS)-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

Chemical Property of (5S,10aS)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,10aS)-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

There total 14 articles about (5S,10aS)-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 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: 71.0%

(5S,10aS)-9-<<5-<(2S-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 (221333-40-0) → (5S,10aS)-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 (221332-83-8)

Guidance literature:

With hydrogenchloride; In methanol; for 8.5h; Ambient temperature;

DOI:10.1248/cpb.47.83

Reference yield:

3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-L-phenylalanine methyl ester (174905-91-0) → (5S,10aS)-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 (221332-83-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / aq. Na₂CO₃ / benzene / 0.5 h / 8 - 10 °C

2: 99 percent / LiBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

3: 93 percent / pyridine / 1.5 h / Ambient temperature

4: 1.) POCl₃, 2.) NaBH₄ / 1.) toluene, reflux, 1.5 h, 2.) MeOH, -78 deg C, 1 h

5: 86 percent / aq. K₂CO₃ / methanol / 1 h / Ambient temperature

6: 91 percent / NaOEt / ethanol / 6 h / Heating

7: 90 percent / anisole, mercuric trifluoroacetate / ethanol / 14.5 h / Ambient temperature

8: 1.) NaH / 1.) DMF, RT, 2.) DMF, 100 deg C, 3 h

9: 82 percent / NaBH₄ / methanol / 1 h / Ambient temperature

10: SOCl₂ / 1 h / Ambient temperature

11: 1.) BuLi, diisopropylamine / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, a) -78 deg C, 2 h, b) -50 deg C, 20 h

12: 71 percent / 0.25N aq. HCl / methanol / 8.5 h / Ambient temperature

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium borohydride; n-butyllithium; thionyl chloride; sodium ethanolate; mercury(II) trifluoroacetate; sodium hydride; sodium carbonate; potassium carbonate; methoxybenzene; diisopropylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; benzene;

DOI:10.1248/cpb.47.83

Reference yield:

N-<(4-methoxyphenyl)acetyl>-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-L-phenylalanine methyl ester (221332-90-7) → (5S,10aS)-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 (221332-83-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / LiBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

2: 93 percent / pyridine / 1.5 h / Ambient temperature

3: 1.) POCl₃, 2.) NaBH₄ / 1.) toluene, reflux, 1.5 h, 2.) MeOH, -78 deg C, 1 h

4: 86 percent / aq. K₂CO₃ / methanol / 1 h / Ambient temperature

5: 91 percent / NaOEt / ethanol / 6 h / Heating

6: 90 percent / anisole, mercuric trifluoroacetate / ethanol / 14.5 h / Ambient temperature

7: 1.) NaH / 1.) DMF, RT, 2.) DMF, 100 deg C, 3 h

8: 82 percent / NaBH₄ / methanol / 1 h / Ambient temperature

9: SOCl₂ / 1 h / Ambient temperature

10: 1.) BuLi, diisopropylamine / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, a) -78 deg C, 2 h, b) -50 deg C, 20 h

11: 71 percent / 0.25N aq. HCl / methanol / 8.5 h / Ambient temperature

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium borohydride; n-butyllithium; thionyl chloride; sodium ethanolate; mercury(II) trifluoroacetate; sodium hydride; potassium carbonate; methoxybenzene; diisopropylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol;

DOI:10.1248/cpb.47.83

upstream raw materials:

(5S,10aS)-9-<<5-<(2S-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

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

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

(S)-N-<2-<3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>phenyl>-1-(hydroxymethyl)ethyl>-4-methoxybenzeneacetamide

Downstream raw materials:

3-methyl-D-histidine

2-amino-3-(3-methyl-3H-imidazol-4-yl)-propionic acid methyl ester

Refernces