4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

Base Information

• Chemical Name: 4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin
• CAS No.: 96680-98-7
• Molecular Formula: C₄₁H₄₅Cl₉N₂O₁₈
• Molecular Weight: 1172.89
• Mol file: 96680-98-7.mol

Synonyms:4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

Chemical Property of 4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

There total 2 articles about 4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin 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:

Carbonic acid (1R,2S,3R,4R,5S,6R)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-6-((2S,3R,4R,6R)-3,4-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,5-bis-(2,2,2-trichloro-ethoxycarbonyloxy)-cyclohexyl ester 2,2,2-trichloro-ethyl ester → 4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin (96680-98-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) p-TsOH; 2.) Dowex-1 (OH-) / benzene / 1 h / 25 °C

2: 270 mg / H₂O / 0.5 h

With Dowex-1 (OH-); toluene-4-sulfonic acid; In water; benzene;

DOI:10.1139/v85-026

Reference yield:

acetic acid (64-19-7,77671-22-8) + Carbonic acid (1R,2S,3R,4R,5S,6R)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-6-((3aR,4S,6R,7aR)-2-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-3,5-bis-(2,2,2-trichloro-ethoxycarbonyloxy)-cyclohexyl ester 2,2,2-trichloro-ethyl ester (96680-99-8) → 4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin (96680-98-7)

Guidance literature:

In water; for 0.5h;

DOI:10.1139/v85-026

Reference yield:

4-O-acetyl-7,9-O-(trichloroethoxycarbonyl)-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin (96680-98-7) → (+)-spectinomycin dihydrochloride (21736-83-4)

Guidance literature:

Multi-step reaction with 5 steps

1: PCC / benzene / 1 h / Heating

2: 60 mg / zinc dust / acetic acid / 30 h / 1.) refux, 1 h, benzene, 2.) glacial ac. acid, 30 h

3: 1.) 1N sodium methoxyde (pH 8); 2.) Dowex-50 (H+) / methanol / 0.25 h / 25 °C

4: 80 percent / 1.) bis(tri-n-butyltin)oxide, 2.)NBS / benzene / 25 °C / 1.) 1 h, 2.) 10 h

5: 90 percent / H₂ / palladium-on-charcoal / H₂O; propan-2-ol

With N-Bromosuccinimide; Dowex-50 (H+); hydrogen; sodium methylate; pyridinium chlorochromate; bis(tri-n-butyltin)oxide; zinc; palladium on activated charcoal; In methanol; water; acetic acid; isopropyl alcohol; benzene;

DOI:10.1139/v85-026

upstream raw materials:

acetic acid

Carbonic acid (1R,2S,3R,4R,5S,6R)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-6-((3aR,4S,6R,7aR)-2-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-3,5-bis-(2,2,2-trichloro-ethoxycarbonyloxy)-cyclohexyl ester 2,2,2-trichloro-ethyl ester

Downstream raw materials:

Acetic acid (2S,4R,6R)-2-[(1R,2R,3S,4R,5R,6S)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-tris-(2,2,2-trichloro-ethoxycarbonyloxy)-cyclohexyloxy]-6-methyl-3-oxo-tetrahydro-pyran-4-yl ester

spectinoic acid

N,N'-<(benzyloxy)carbonyl>actinamine

N,N'<(benzyloxy)carbonyl>spectinoid acid lactone

Refernces