(2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine

Base Information

• Chemical Name: (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine
• CAS No.: 228997-18-0
• Molecular Formula: C₃₈H₄₂N₂O₅S
• Molecular Weight: 638.828

Synonyms:(2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine

Chemical Property of (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine

Chemical Property:

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Technology Process of (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine

There total 11 articles about (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine 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:

3,5-Dihydroxybenzoic acid (99-10-5) → (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine (228997-18-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1) DMF, 1.3 h; 2) DMF, rt, 27 h

2: aq. NaOH / methanol / 3 h / Ambient temperature

3: 90 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / 2 h

4: 1.) sec-BuLi, TMEDA, 2.) sulfur / 1) THF, cyclohexane, -78 deg C, 1 h; 2) THF, cyclohexane, 0 deg C, 1.5 h; 3) THF, cyclohexane, 0 deg C, 2 h

5: 87 percent / aq. HCl / methanol / 2.5 h / 60 - 64 °C

6: 1.) NaH / 1) DMF, rt, 1 h; 2) DMF, 0 deg C, 10 min, rt, 4.5 h

7: 97 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 35 min; 2) reflux, 3 h

8: 80 percent / ethyl chloroformate / benzene / 23 h / Ambient temperature

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

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diethyl cyanophosphonate; sec.-butyllithium; chloroformic acid ethyl ester; sodium hydride; sulfur; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene;

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

Reference yield:

benzyl bromide (100-39-0) → (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine (228997-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1) DMF, rt, 1 h; 2) DMF, 0 deg C, 10 min, rt, 4.5 h

2: 97 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 35 min; 2) reflux, 3 h

3: 80 percent / ethyl chloroformate / benzene / 23 h / Ambient temperature

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

With lithium aluminium tetrahydride; n-butyllithium; chloroformic acid ethyl ester; sodium hydride; diisopropylamine; In tetrahydrofuran; benzene;

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

Reference yield:

methyl 3,5-bis(methoxymethoxy)benzoate (76280-59-6) → (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine (228997-18-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Me₃Al / 1) toluene, hexane, -25 deg C, 20 min, rt, 45 min; 2) toluene, hexane, reflux, 18 h

2: 1.) sec-BuLi, TMEDA, 2.) sulfur / 1) THF, cyclohexane, -78 deg C, 1 h; 2) THF, cyclohexane, 0 deg C, 1.5 h; 3) THF, cyclohexane, 0 deg C, 2 h

3: 87 percent / aq. HCl / methanol / 2.5 h / 60 - 64 °C

4: 1.) NaH / 1) DMF, rt, 1 h; 2) DMF, 0 deg C, 10 min, rt, 4.5 h

5: 97 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 35 min; 2) reflux, 3 h

6: 80 percent / ethyl chloroformate / benzene / 23 h / Ambient temperature

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

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; trimethylaluminum; sec.-butyllithium; chloroformic acid ethyl ester; sodium hydride; sulfur; diisopropylamine; In tetrahydrofuran; methanol; benzene;

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

upstream raw materials:

(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

3,5-bis(benzyloxy)-1-(chloromethyl)-2-<<(4-methoxxyphenyl)methyl>thio>benzene

3,5-Dihydroxybenzoic acid

benzyl bromide

Downstream raw materials:

(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-<<(4-methoxyphenyl)methyl>thio>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

(1R,3R)-6,8-bis(benzyloxy)-1-<(4-(benzyloxy)phenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

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

N-<<4-(benzyloxy)phenyl>acetyl>-3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester

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