t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate

Base Information

• Chemical Name: t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate
• CAS No.: 138395-26-3
• Molecular Formula: C₃₄H₅₃N₃O₅
• Molecular Weight: 583.812
• Mol file: 138395-26-3.mol

Synonyms:t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate

Chemical Property of t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate

There total 2 articles about t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate 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: 45.0%

t-Butyl (S,S)-N-<4-<4-(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methylpyrrol-2-yl>-5,5-dimethyl-1-thioxo-3,6-heptadienyl>-N-methylvalinate (138372-12-0) → Bis(2-methoxycarbonylbenzyl) sulfide (89066-57-9) + t-Butyl (S,S)-N-<3-(2-t-butoxycarbonylamino-3-hydroxypropyl)-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate (138395-27-4) + (S)-4-[7-(1,1-Dimethyl-allyl)-4-(2-methoxycarbonyl-benzylsulfanyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (138372-14-2) + t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate (138395-26-3)

Guidance literature:

With methyl 2-bromomethylbenzoate; 2-methyl-but-2-ene; In N,N-dimethyl-formamide; at 45 ℃; for 6.66667h; Further byproducts given;

DOI:10.1016/S0040-4020(01)88285-5

Reference yield: 45.0%

methyl 2-bromomethylbenzoate (2417-73-4) + t-Butyl (S,S)-N-<4-<4-(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methylpyrrol-2-yl>-5,5-dimethyl-1-thioxo-3,6-heptadienyl>-N-methylvalinate (138372-12-0) → Bis(2-methoxycarbonylbenzyl) sulfide (89066-57-9) + t-Butyl (S,S)-N-<3-(2-t-butoxycarbonylamino-3-hydroxypropyl)-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate (138395-27-4) + (S)-4-[7-(1,1-Dimethyl-allyl)-4-(2-methoxycarbonyl-benzylsulfanyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (138372-14-2) + t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate (138395-26-3)

Guidance literature:

With 2-methyl-but-2-ene; In N,N-dimethyl-formamide; at 45 ℃; for 6.66667h; Further byproducts given;

DOI:10.1016/S0040-4020(01)88285-5

Reference yield:

t-Butyl (S,S)-N-<3-<(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)-methyl>-7-(2-methyl-3-buten-2-yl)-4-indolyl>-N-methylvalinate (138395-26-3) → (-)-pendolmycin (119375-01-8,138512-90-0)

Guidance literature:

With triethylamine; diethyl dicarbonate; trifluoroacetic acid; Yield given. Multistep reaction; 1.) 24 deg C, 17.5 h, 2.) DMF, 24 deg C, 17.5 h;

DOI:10.1016/S0040-4020(01)88285-5

upstream raw materials:

methyl 2-bromomethylbenzoate

t-Butyl (S,S)-N-<4-<4-(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methylpyrrol-2-yl>-5,5-dimethyl-1-thioxo-3,6-heptadienyl>-N-methylvalinate

Downstream raw materials:

(-)-pendolmycin