(4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one

Base Information

• Chemical Name: (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one
• CAS No.: 176847-64-6
• Molecular Formula: C₂₇H₃₃N₇O₇
• Molecular Weight: 567.602
• Mol file: 176847-64-6.mol

Synonyms:(4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one

Chemical Property of (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one

There total 4 articles about (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one 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: 51.0%

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine (34245-49-3) + (S)-4-(2-Iodo-ethyl)-oxazolidin-5-one → (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one (176847-64-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 55 ℃; for 48h;

DOI:10.1039/cc9960000791

Reference yield: 51.0%

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine (34245-49-3) + (4S)-N-benzyloxycarbonyl-4-(2-iodoethyl)oxazolidin-5-one (118762-77-9) → (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one (176847-64-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 55 ℃; for 48h;

DOI:10.1135/cccc19960085

Reference yield:

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester (58456-26-1) → (4S)-N-benzyloxycarbonyl-4-[2-[N-2',3'-O,O-(1-methylethylidene)adenosyl-N-methyl]aminoethyl]oxazolidin-5-one (176847-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / 2,2,2-trifluoro-1-iodoethane; N-hydroxypyridine-2-thione sodium salt; DMAP / CH₂Cl₂ / 1.17 h / Heating; irradiation

2: 51 percent / N,N-diisopropylethylamine / acetonitrile / 48 h / 55 °C

With dmap; 1,1,1-trifluoro-2-iodoethane; 2-mercaptopyridine-1-oxide sodium salt; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; 1: Iodination / 2: Substitution;

DOI:10.1021/jo9907742

upstream raw materials:

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine

(4S)-N-benzyloxycarbonyl-4-(2-iodoethyl)oxazolidin-5-one

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

Downstream raw materials:

5'-[N-[(3S)-3-amino-3-carboxypropyl]-N-methylamino]-5'-deoxyadenosine