(-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

Base Information

Chemical Name:(-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate
CAS No.:219739-58-9
Molecular Formula:C₁₅H₁₉NO₆
Molecular Weight:309.319
Hs Code.:

Synonyms:(-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

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Chemical Property of (-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

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Technology Process of (-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

There total 6 articles about (-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate 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:

: 219739-56-7
(-)-methyl (1R,3R,4S,5R)-1-(benzoyloxy)-5-(N,N-dibenzylamino)-3,4-dihydroxycyclohexane carboxylate

: 219739-58-9
(-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

Guidance literature:: With formic acid; palladium; In methanol; for 0.5h; Yield given;
DOI:10.1021/jo981291l

Reference yield:

: 1-O-benzoyl-4,5-O-isopropylidenequinide

: 219739-58-9
(-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: methanol / 0.5 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: CF₃COOH / tetrahydrofuran; H₂O / 0 - 20 °C

4: 80 percent / DBU, LiBr / tetrahydrofuran / 0.17 h / 0 - 20 °C

5: 40 percent / Ti(OiPr)4 / 48 h / Ambient temperature

6: formic acid / palladium black / methanol / 0.5 h

With pyridine; titanium(IV) isopropylate; formic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium bromide; palladium; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo981291l

Reference yield:

: 219739-55-6
(-)-methyl (1S,3R,4R,5R)-1-(benzoyloxy)-3,4-epoxy-5-hydroxycyclohexane carboxylate

: 219739-58-9
(-)-methyl (1R,3R,4S,5R)-5-amino-1-(benzoyloxy)-3,4-dihydroxycyclohexane carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 40 percent / Ti(OiPr)4 / 48 h / Ambient temperature

2: formic acid / palladium black / methanol / 0.5 h

With titanium(IV) isopropylate; formic acid; palladium; In methanol;
DOI:10.1021/jo981291l