2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

Base Information

Chemical Name:2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B
CAS No.:133036-52-9
Molecular Formula:C₅₉H₉₀FN₅O₂₀S₂
Molecular Weight:1272.52
Hs Code.:

2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

Synonyms:

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Chemical Property of 2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

Chemical Property:

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Safty Information:

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Useful:

Technology Process of 2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

There total 7 articles about 2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B 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:

: 133036-51-8,133099-22-6
6',2''-bis(O-benzylsulfonyl)-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(tosylaminomethyl)kanamycin C

: 133036-52-9,133099-23-7
2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

Guidance literature:: With potassium hydrogen bifluoride; In N,N-dimethyl-formamide; at 120 ℃; for 4h; Yield given; sealed tube;
DOI:10.1246/bcsj.63.3583

Reference yield:

: 72908-98-6
1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-3',4',6'-trideoxy-4'',6''-O-isopropylidene-6'-oxokanamycin C

: 133036-52-9,133099-23-7
2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

Guidance literature:: Multi-step reaction with 6 steps

1: sodium methoxide / methanol / 1 h / Ambient temperature

2: hydrogen / PtO₂ / methanol; H₂O; acetic acid / 120 h / 2942.03 Torr / Ambient temperature

3: sodium carbonate / dioxane; H₂O / 1 h / Ambient temperature

4: p-toluenesulfonic acid monohydrate / dimethylformamide / 13 h / Ambient temperature

5: pyridine / 1 h / 0 - 5 °C

6: KHF₂ / dimethylformamide / 4 h / 120 °C / sealed tube

With pyridine; potassium hydrogen bifluoride; hydrogen; sodium methylate; sodium carbonate; toluene-4-sulfonic acid; platinum(IV) oxide; In 1,4-dioxane; methanol; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.63.3583

Reference yield:

: 133036-47-2,133099-25-9
1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-3',4'-dideoxy-6'-C-(nitromethyl)kanamycin C

: 133036-52-9,133099-23-7
2''-O-benzylsulfonyl-1,3,2',3''-tetrakis(N-t-butoxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxy-6'-C-(fluoromethyl)-6'-N-tosylkanamycin B

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen / PtO₂ / methanol; H₂O; acetic acid / 120 h / 2942.03 Torr / Ambient temperature

2: sodium carbonate / dioxane; H₂O / 1 h / Ambient temperature

3: p-toluenesulfonic acid monohydrate / dimethylformamide / 13 h / Ambient temperature

4: pyridine / 1 h / 0 - 5 °C

5: KHF₂ / dimethylformamide / 4 h / 120 °C / sealed tube

With pyridine; potassium hydrogen bifluoride; hydrogen; sodium carbonate; toluene-4-sulfonic acid; platinum(IV) oxide; In 1,4-dioxane; methanol; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.63.3583