(3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

Base Information

• Chemical Name: (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene
• CAS No.: 195325-66-7
• Molecular Formula: C₂₇H₃₄N₂O₅S
• Molecular Weight: 498.643
• Mol file: 195325-66-7.mol

Synonyms:(3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

Chemical Property of (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

There total 4 articles about (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene 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:

Boc-Trp-OH (13139-14-5) → (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 4-dimethylaminopyridine, N,N-dicyclohexylcarbodiimide, N,N-diisopropylethylamine / CH₂Cl₂ / 1.) from -30 to -20 deg C, 2 h, 2.) RT, 16 h

2: 1.) NaH / 1.) DMF, 0 deg C, 2 h, 2.) DMF, a) 0 deg C, 3 h, b) RT, 15 h

3: 1 M DIBAL / toluene; tetrahydrofuran / 1.5 h / -78 °C

4: tetrahydrofuran / 20 h / 0 °C

With dmap; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1248/cpb.45.1259

Reference yield:

(S)-tert-butyl (3-(1H-indol-3-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (97530-05-7) → (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2 h, 2.) DMF, a) 0 deg C, 3 h, b) RT, 15 h

2: 1 M DIBAL / toluene; tetrahydrofuran / 1.5 h / -78 °C

3: tetrahydrofuran / 20 h / 0 °C

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1248/cpb.45.1259

Reference yield:

{(S)-1-(Methoxy-methyl-carbamoyl)-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (195325-55-4) → (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 M DIBAL / toluene; tetrahydrofuran / 1.5 h / -78 °C

2: tetrahydrofuran / 20 h / 0 °C

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1248/cpb.45.1259

upstream raw materials:

vinylmagnesium chloride

{(S)-1-Formyl-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester

Boc-Trp-OH

(S)-tert-butyl (3-(1H-indol-3-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

Downstream raw materials:

(3R,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene

(3S,4S)-4-tert-butyloxycarbonylamino-1,2-dihydroxy-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolylpentane

(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester

(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-(tetrahydro-pyran-2-yloxy)-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester