(3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester

Base Information

• Chemical Name: (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester
• CAS No.: 318466-96-5
• Molecular Formula: C₃₇H₅₃BrN₄O₁₀S₂
• Molecular Weight: 857.885

Synonyms:(3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester

Chemical Property of (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester

There total 16 articles about (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl 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:

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid (77856-52-1) → (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester (318466-96-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogen / Pd/C / methanol / 1 h / 20 °C / 760 Torr

1.2: 7.7 g / triethylamine / methanol / 0.17 h / 20 °C

2.1: 5.9 g / DCC; DMAP / acetonitrile / 1 h / 20 °C

3.1: triethylsilane / Pd/C / acetone / 0.5 h / 20 °C

4.1: 5.08 g / tetrahydrofuran / -78 - 20 °C

5.1: thionyl chloride / methanol / 0.5 h / 20 °C

6.1: 3.5 g / triethylamine / CH₂Cl₂ / 0.17 h / 20 °C

7.1: Ph₃P; DEAD / benzene; toluene / 0.17 h / 20 °C

8.1: 312 mg / Ti(OiPr)4 / 15 h / 95 °C

With titanium(IV) isopropylate; triethylsilane; dmap; thionyl chloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile; benzene; 4.1: Wittig reaction / 7.1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00626-9

Reference yield:

(3S)-3-tert-butoxycarbonylamino-4-methoxycarbonyl-butyric acid (82803-56-3) → (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester (318466-96-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 5.9 g / DCC; DMAP / acetonitrile / 1 h / 20 °C

2: triethylsilane / Pd/C / acetone / 0.5 h / 20 °C

3: 5.08 g / tetrahydrofuran / -78 - 20 °C

4: thionyl chloride / methanol / 0.5 h / 20 °C

5: 3.5 g / triethylamine / CH₂Cl₂ / 0.17 h / 20 °C

6: Ph₃P; DEAD / benzene; toluene / 0.17 h / 20 °C

7: 312 mg / Ti(OiPr)4 / 15 h / 95 °C

With titanium(IV) isopropylate; triethylsilane; dmap; thionyl chloride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile; benzene; 3: Wittig reaction / 6: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00626-9

Reference yield:

(3R)-3-tert-butoxycarbonylamino-4-ethylsulfanylcarbonyl-butyric acid methyl ester (318466-91-0) → (3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid allyl ester (318466-96-5)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylsilane / Pd/C / acetone / 0.5 h / 20 °C

2: 5.08 g / tetrahydrofuran / -78 - 20 °C

3: thionyl chloride / methanol / 0.5 h / 20 °C

4: 3.5 g / triethylamine / CH₂Cl₂ / 0.17 h / 20 °C

5: Ph₃P; DEAD / benzene; toluene / 0.17 h / 20 °C

6: 312 mg / Ti(OiPr)4 / 15 h / 95 °C

With titanium(IV) isopropylate; triethylsilane; thionyl chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; benzene; 2: Wittig reaction / 5: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00626-9

upstream raw materials:

allyl alcohol

(3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid methyl ester

1,5-dibromo-pentane

n-nonylidene triphenylphosphorane

Downstream raw materials:

(3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid

C₃₉H₅₇BrN₄O₁₁S₂

(8S,2Z)-1,9,13-tris(2-nitrobenzenesulfonyl)-8-(undec-2-enyl)-1,5,9,13-tetraazacyclooctadecan-6-one

(3S,5Z)-3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]tetradec-5-enoic acid [3-(2-nitrobenzenesulfonylamino)propyl]amide

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