methyl (E)-7-[1-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-(dimethylamino)cyclopentyl]hept-5-enoate

Base Information

• Chemical Name: methyl (E)-7-[1-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-(dimethylamino)cyclopentyl]hept-5-enoate
• CAS No.: 77506-98-0
• Molecular Formula: C41H73NO6SSi2
• Molecular Weight: 764.271
• NSC Number: 370789

Synonyms:NSC370789;77506-98-0;NSC-370789

Chemical Property of methyl (E)-7-[1-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-(dimethylamino)cyclopentyl]hept-5-enoate

Chemical Property:

• Vapor Pressure: 2.43E-20mmHg at 25°C
• Boiling Point: 715.8°Cat760mmHg
• Flash Point: 386.7°C
• Density: 1.03g/cm³
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 22
• Exact Mass: 763.46971329
• Heavy Atom Count: 51
• Complexity: 1240

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1(CC=CCCCC(=O)OC)S(=O)(=O)C2=CC=CC=C2)N(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CCCCCC(/C=C/C1C(CC(C1(C/C=C/CCCC(=O)OC)S(=O)(=O)C2=CC=CC=C2)N(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C

Technology Process of methyl (E)-7-[1-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-(dimethylamino)cyclopentyl]hept-5-enoate

There total 4 articles about methyl (E)-7-[1-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-(dimethylamino)cyclopentyl]hept-5-enoate 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:

methyl (5Z)-7-bromo-5-heptenoate (51751-83-8) + (S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene (41138-68-5) + (1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene (77493-70-0) → Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77506-98-0) + (1S,2S,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-trans-2-(phenylsulfonyl)cyclopentane (77494-46-3) + (1S,2R,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-cis-2-(phenylsulfonyl)cyclopentane (77520-22-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/ja00398a048

Reference yield:

methyl (5Z)-7-iodo-5-heptenoate (64493-06-7) + (S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene (41138-68-5) + (1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene (77493-70-0) → Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77506-98-0) + (1S,2S,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-trans-2-(phenylsulfonyl)cyclopentane (77494-46-3) + (1S,2R,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-cis-2-(phenylsulfonyl)cyclopentane (77520-22-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C, 2.) -40 deg C -> 0 deg C, 1 h;

DOI:10.1021/ja00398a048

Reference yield:

methyl (5Z)-7-bromo-5-heptenoate (51751-83-8) + (S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene (41138-68-5) + (1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene (77493-70-0) → Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (85548-77-2) + Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77506-98-0) + (1S,2S,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-trans-2-(phenylsulfonyl)cyclopentane (77494-46-3) + (1S,2R,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-cis-2-(phenylsulfonyl)cyclopentane (77520-22-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo00161a010

upstream raw materials:

methyl (5Z)-7-bromo-5-heptenoate

(S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene

(1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene

methyl (5Z)-7-iodo-5-heptenoate

Downstream raw materials:

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-<methylamino>-8-(phenylsulfonyl)-5,13-prostadienoate

Methyl (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoate

(Z)-7-[(1R,2S,3R,5S)-1-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-(methyl-phenoxycarbonyl-amino)-cyclopentyl]-hept-5-enoic acid

(Z)-7-[(1R,2S,3R,5S)-1-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-(ethoxycarbonyl-methyl-amino)-cyclopentyl]-hept-5-enoic acid

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