(5R,10aR)-9-mercapto-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-mercapto-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one
• CAS No.: 213692-63-8
• Molecular Formula: C₂₁H₂₃NO₅S
• Molecular Weight: 401.483

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

There total 8 articles about (5R,10aR)-9-mercapto-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-mercapto-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one (213692-63-8)

Guidance literature:

Multi-step reaction with 7 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

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

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

Reference yield:

3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester (213692-58-1) → (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)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent

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

3: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

4: 98 percent / NaOEt / ethanol / 20 h / Heating

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

With sodium tetrahydroborate; lithium aluminium tetrahydride; Hexamethyldisiloxane; sodium ethanolate; mercury(II) trifluoroacetate; phosphorus pentoxide; methoxybenzene; In tetrahydrofuran; ethanol;

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

Reference yield:

(1R,3R)-3-hydroxymethyl-6,8-dimethoxy-1-<(4-methoxyphenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline (213692-61-6) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaOEt / ethanol / 20 h / Heating

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

With sodium tetrahydroborate; sodium ethanolate; mercury(II) trifluoroacetate; methoxybenzene; In ethanol;

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

upstream raw materials:

(5R,10aR)-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-9-<<(4-methoxyphenyl)methyl>thio>-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

(1R,3R)-3-hydroxymethyl-6,8-dimethoxy-1-<(4-methoxyphenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

(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

(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

(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

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