(1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Base Information

Chemical Name:(1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol
CAS No.:179094-14-5
Molecular Formula:C₂₈H₃₄N₂O₈
Molecular Weight:526.587
Hs Code.:

Synonyms:(1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

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Chemical Property of (1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

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Technology Process of (1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

There total 9 articles about (1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol 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:

: 1053711-13-9
{(R)-1-[(2R,3R)-3-((R)-1-Benzyloxycarbonylamino-2-oxo-ethyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

: 179094-14-5
(1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Guidance literature:: With 2; N,N-dimethyl-formamide; In dichloromethane; for 3h;
DOI:10.1021/jo960691a

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 179094-14-5
(1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / imidazole / dimethylformamide / 8 h

2: 94 percent / CaCl₂, NaBH₄ / tetrahydrofuran; ethanol / 0 deg C -> room temperature, 3 h

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -63 deg C, 30 min, 2.) -63 deg C, 30 min

4: 97 percent / 2Cl₃(THF)6>22Cl₆> / CH₂Cl₂ / 4 h

5: 99 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating

6: 1.93 g / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -63 deg C, 30 min, 2.) -63 deg C, 30 min

8: 0.71 g / 2Cl₃(THF)6>22Cl₆>, DMF / CH₂Cl₂ / 3 h

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; 2; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo960691a

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 179094-14-5
(1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / K₂CO₃*1.5H₂O / H₂O; tetrahydrofuran / 0 deg C -> room temperature, 4 h

2: 96 percent / imidazole / dimethylformamide / 8 h

3: 94 percent / CaCl₂, NaBH₄ / tetrahydrofuran; ethanol / 0 deg C -> room temperature, 3 h

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -63 deg C, 30 min, 2.) -63 deg C, 30 min

5: 97 percent / 2Cl₃(THF)6>22Cl₆> / CH₂Cl₂ / 4 h

6: 99 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating

7: 1.93 g / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

8: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -63 deg C, 30 min, 2.) -63 deg C, 30 min

9: 0.71 g / 2Cl₃(THF)6>22Cl₆>, DMF / CH₂Cl₂ / 3 h

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; 2; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo960691a