Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester
CAS No.:95058-22-3
Molecular Formula:C₃₀H₂₉F₃N₂O₁₀S
Molecular Weight:666.629
Hs Code.:

Synonyms:Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

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Chemical Property of Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

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Technology Process of Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

There total 7 articles about Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl 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: 95.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 95058-21-2
D,L-(1r,2c,3c,4t,6t)-4-O-benzoyl-3,6-bis(benzyloxycarbonylamino)-1,2,4-cyclohexanetriol

: 95058-22-3
Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

Guidance literature:: With pyridine; at 0 ℃; for 3h;
DOI:10.1246/cl.1984.1665

Reference yield:

: 98-88-4
benzoyl chloride

: 95058-22-3
Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / pyridine / 21 h / Ambient temperature

2: 70 percent / pyridine

3: 93 percent / AcOH, H₂O / 2 h / 80 °C

4: 98 percent / NaI / dimethylformamide / 8 h / 100 °C

5: 96 percent / tri-n-butyl tin hydride, AIBN / tetrahydrofuran / Heating

6: 95 percent / pyridine / 3 h / 0 °C

With pyridine; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; acetic acid; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1246/cl.1984.1665

Reference yield:

: 95058-16-5
D,L-(1r,2c,3c,4t,5t,6t)-1,4-bis(benzyloxycarbonylamino)-2,3-O-isopropyylidene-2,3,5,6-cyclohexanetetraol

: 95058-22-3
Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / pyridine / 21 h / Ambient temperature

2: 70 percent / pyridine

3: 93 percent / AcOH, H₂O / 2 h / 80 °C

4: 98 percent / NaI / dimethylformamide / 8 h / 100 °C

5: 96 percent / tri-n-butyl tin hydride, AIBN / tetrahydrofuran / Heating

6: 95 percent / pyridine / 3 h / 0 °C

With pyridine; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; acetic acid; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1246/cl.1984.1665