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

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Chemical Name:(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol
CAS No.:179094-15-6
Molecular Formula:C₂₁H₂₆N₂O₇
Molecular Weight:418.447
Hs Code.:

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

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

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

There total 10 articles about (1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-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: 51.0%

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

: 179094-15-6
(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Guidance literature:: With sodium carbonate; In 1,4-dioxane; water;
DOI:10.1021/jo960691a

Reference yield:

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

: 179094-15-6
(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 9 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

9: 51 percent / Na₂CO₃ / dioxane; H₂O

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

Reference yield:

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

: 179094-15-6
(1S,2S,3R,4R,5S,6R)-5-amino-2-[N-(benzyloxycarbonyl)amino]-5-N,6-O-carbonyl-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 10 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

10: 51 percent / Na₂CO₃ / dioxane; H₂O

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