(-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

Base Information

Chemical Name:(-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol
CAS No.:121467-92-3
Molecular Formula:C₁₇H₂₂N₂O₆
Molecular Weight:350.371
Hs Code.:

Synonyms:(-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

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Chemical Property of (-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

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Technology Process of (-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

There total 9 articles about (-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol 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%

: 121467-84-3
(3aR,4S,6S,7R,7aR)-6-Amino-7-hydroxy-4-methoxy-3-methyl-hexahydro-benzooxazol-2-one

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

: 121467-92-3
(-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

Guidance literature:: With sodium carbonate; In water; acetone; for 3h;
DOI:10.1016/S0040-4039(01)91038-X

Reference yield:

: 94592-12-8
DL-(1α,2α,3β,4β,5α)-1,2-anhydro-3-O,4-N-carbonyl-4-(methylamino)-1,2,3,5-cyclohexanetetrol

: 121467-92-3
(-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / NaH / dimethylformamide / 1 h / 0 °C

2: 47 percent / propan-1-ol / 12 h / Heating

3: conc. H₂SO₄, H₂ / Pd/C / methanol / 6 h / Ambient temperature

4: Na₂CO₃ / methanol; H₂O / 0 deg C, 45 min; RT, 0.5 h

With sulfuric acid; hydrogen; sodium hydride; sodium carbonate; palladium on activated charcoal; In methanol; propan-1-ol; water; N,N-dimethyl-formamide;

Reference yield:

: 94592-11-7
(1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-3-O-(methylcarbamoyl)-1,2,3,4,5-cyclohexane-pentol

: 121467-92-3
(-)-(1R)-(1α,2β,3β,4α,6β)-6-<(benzyloxycarbonyl)amino>-2-O,3-N-carbonyl-4-O-methyl-3-(methylamino)-1,2,4-cyclohexanetriol

Guidance literature:: Multi-step reaction with 5 steps

1: chiral phase transfer catalyst, KOH / dioxane / 23 °C

2: 94 percent / NaH / dimethylformamide / 1 h / 0 °C

3: 47 percent / propan-1-ol / 12 h / Heating

4: conc. H₂SO₄, H₂ / Pd/C / methanol / 6 h / Ambient temperature

5: Na₂CO₃ / methanol; H₂O / 0 deg C, 45 min; RT, 0.5 h

With potassium hydroxide; chiral phase transfer catalyst; sulfuric acid; hydrogen; sodium hydride; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; propan-1-ol; water; N,N-dimethyl-formamide;