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

Base Information

• Chemical Name: 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
• CAS No.: 96680-99-8
• Molecular Formula: C₄₂H₄₇Cl₉N₂O₁₈
• Molecular Weight: 1186.91
• Mol file: 96680-99-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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:

Trimethyl orthoacetate (1445-45-0) + 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 → 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)

Guidance literature:

With Dowex-1 (OH-); toluene-4-sulfonic acid; In benzene; at 25 ℃; for 1h;

DOI:10.1139/v85-026

Reference yield:

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) → (+)-spectinomycin dihydrochloride (21736-83-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 270 mg / H₂O / 0.5 h

2: PCC / benzene / 1 h / Heating

3: 60 mg / zinc dust / acetic acid / 30 h / 1.) refux, 1 h, benzene, 2.) glacial ac. acid, 30 h

4: 1.) 1N sodium methoxyde (pH 8); 2.) Dowex-50 (H+) / methanol / 0.25 h / 25 °C

5: 80 percent / 1.) bis(tri-n-butyltin)oxide, 2.)NBS / benzene / 25 °C / 1.) 1 h, 2.) 10 h

6: 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

Reference yield:

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) → spectinomycin free base (1695-77-8,68889-81-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 270 mg / H₂O / 0.5 h

2: PCC / benzene / 1 h / Heating

3: 60 mg / zinc dust / acetic acid / 30 h / 1.) refux, 1 h, benzene, 2.) glacial ac. acid, 30 h

4: 1.) 1N sodium methoxyde (pH 8); 2.) Dowex-50 (H+) / methanol / 0.25 h / 25 °C

5: 80 percent / 1.) bis(tri-n-butyltin)oxide, 2.)NBS / benzene / 25 °C / 1.) 1 h, 2.) 10 h

6: 90 percent / H₂ / palladium-on-charcoal / H₂O; propan-2-ol

7: Dowex-1 (OH-)

With N-Bromosuccinimide; Dowex-1 (OH-); 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:

Trimethyl orthoacetate

Downstream raw materials:

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

spectinoic acid

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

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

Refernces