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

Base Information

• Chemical Name: (3R,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene
• CAS No.: 195325-67-8
• Molecular Formula: C₃₂H₄₂N₂O₆S
• Molecular Weight: 582.761
• Mol file: 195325-67-8.mol

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

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

There total 4 articles about (3R,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-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: 85.0%

3,4-dihydro-2H-pyran (110-87-2) + (3R,4S)-4-tert-butyloxycarbonylamino-3-hydroxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-66-7) → (3R,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-67-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.45.1259

Reference yield:

Boc-Trp-OH (13139-14-5) → (3R,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-67-8)

Guidance literature:

Multi-step reaction with 5 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

5: 85 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1248/cpb.45.1259

Reference yield:

{(S)-1-Formyl-2-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (1026493-36-6) → (3R,4S)-4-tert-butyloxycarbonylamino-3-tetrahydropyranyloxy-5-3'-(N-mesitylene-2-sulfonyl)indolyl-1-pentene (195325-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 20 h / 0 °C

2: 85 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

With toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.45.1259

upstream raw materials:

3,4-dihydro-2H-pyran

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

Boc-Trp-OH

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

Downstream raw materials:

(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

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

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