ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

Base Information

Chemical Name:ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone
CAS No.:390747-37-2
Molecular Formula:C₂₂H₃₂N₂O₇
Molecular Weight:436.505
Hs Code.:

Synonyms:ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

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Chemical Property of ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

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Technology Process of ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

There total 7 articles about ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone 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:

: 390747-32-7
ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-4-O-tert-butyldiphenylsilyl-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

: 390747-37-2
ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4020(01)00865-1

Reference yield:

: 114743-85-0
methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

: 390747-37-2
ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / imidazole / dimethylformamide / 12 h / 60 °C

2: 70 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

3: DCC / CH₂Cl₂ / 1 h / 0 °C

4: CH₂Cl₂ / 1 h / -30 °C / Photolysis

5: pyridine / CH₂Cl₂ / 12 h / -20 - 20 °C

6: TBAF / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00865-1

Reference yield:

: 77-76-9
2,2-dimethoxy-propane

: 390747-37-2
ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / acetone; p-toluenesulphonic acid / methanol / 18 h / 20 °C

2: 95 percent / imidazole / dimethylformamide / 12 h / 60 °C

3: 70 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

4: DCC / CH₂Cl₂ / 1 h / 0 °C

5: CH₂Cl₂ / 1 h / -30 °C / Photolysis

6: pyridine / CH₂Cl₂ / 12 h / -20 - 20 °C

7: TBAF / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; acetone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00865-1