(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

Base Information

• Chemical Name: (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
• CAS No.: 228997-16-8
• Molecular Formula: C₃₈H₅₂N₄O₁₀S
• Molecular Weight: 756.918
• Mol file: 228997-16-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (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 (228997-15-7) → (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 (228997-16-8)

Guidance literature:

In chloroform; for 6h; Ambient temperature;

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

Reference yield:

1-(chloromethyl)-3,5-dimethoxy-2-{[(4-methoxyphenyl)methyl]thio}benzene (174905-86-3) → (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 (228997-16-8)

Guidance literature:

Multi-step reaction with 15 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

11: 90 percent / aq. HCl / methanol / 2.5 h / Ambient temperature

12: aq. HCl / 1 h / 100 °C

13: aq. NaOH / methanol / 60 h / 80 - 85 °C

14: HCl / 7 h / Heating

15: 97 percent / CHCl₃ / 6 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; 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; chloroform; N,N-dimethyl-formamide;

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) → (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 (228997-16-8)

Guidance literature:

Multi-step reaction with 13 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

6: 68 percent / NaH / dimethylformamide / 3.25 h / 100 °C

7: 80 percent / NaBH₄ / methanol / 1 h / Ambient temperature

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

9: 90 percent / aq. HCl / methanol / 2.5 h / Ambient temperature

10: aq. HCl / 1 h / 100 °C

11: aq. NaOH / methanol / 60 h / 80 - 85 °C

12: HCl / 7 h / Heating

13: 97 percent / CHCl₃ / 6 h / Ambient temperature

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

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

upstream raw materials:

di-tert-butyl dicarbonate

(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

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)-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