(S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester
• CAS No.: 292157-39-2
• Molecular Formula: C₄₂H₅₂INO₆SSi
• Molecular Weight: 853.934

Synonyms:(S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester

Chemical Property of (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester

There total 13 articles about (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid 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: 66.0%

(S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-hydroxy-butoxy)-phenyl]-propionic acid methyl ester (292157-37-0) → (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester (292157-39-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; methyl iodide; In toluene;

DOI:10.1016/S0040-4039(00)00709-7

Reference yield:

(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid (4703-32-6) → (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester (292157-39-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / diethyl ether

2: 98 percent / PPTS / CH₂Cl₂

3: 75 percent / DEAD; Ph₃P / tetrahydrofuran

4: 71 percent / PTSA / CH₂Cl₂; propan-2-ol

5: 81 percent / DEAD; Ph₃P / tetrahydrofuran

6: 77 percent / PPTS / CH₂Cl₂; methanol

7: 66 percent / DEAD; Ph₃P; MeI / toluene

With pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; isopropyl alcohol; toluene; 1: Esterification / 2: Etherification / 3: Mitsunobu reaction / 4: Hydrolysis / 5: Mitsunobu reaction / 6: Hydrolysis / 7: Iodination;

DOI:10.1016/S0040-4039(00)00709-7

Reference yield:

N-tosyl L-tyrosine methyl ester (101585-61-9) → (S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-iodo-butoxy)-phenyl]-propionic acid methyl ester (292157-39-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / PPTS / CH₂Cl₂

2: 75 percent / DEAD; Ph₃P / tetrahydrofuran

3: 71 percent / PTSA / CH₂Cl₂; propan-2-ol

4: 81 percent / DEAD; Ph₃P / tetrahydrofuran

5: 77 percent / PPTS / CH₂Cl₂; methanol

6: 66 percent / DEAD; Ph₃P; MeI / toluene

With pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol; toluene; 1: Etherification / 2: Mitsunobu reaction / 3: Hydrolysis / 4: Mitsunobu reaction / 5: Hydrolysis / 6: Iodination;

DOI:10.1016/S0040-4039(00)00709-7

upstream raw materials:

(S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-3-[4-(4-hydroxy-butoxy)-phenyl]-propionic acid methyl ester

(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid

N-tosyl L-tyrosine methyl ester

L-tyrosine

Downstream raw materials:

2-[4-(4-{(S)-2-[[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-2-methoxycarbonyl-ethyl}-phenoxy)-butyl]-malonic acid dimethyl ester

2-[4-(4-{(S)-2-[((E)-5-Chloro-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-2-methoxycarbonyl-ethyl}-phenoxy)-butyl]-malonic acid dimethyl ester

2-[4-(4-{(S)-2-[((E)-5-Hydroxy-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-2-methoxycarbonyl-ethyl}-phenoxy)-butyl]-malonic acid dimethyl ester

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