methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

Base Information

Chemical Name:methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate
CAS No.:1289557-72-7
Molecular Formula:C₁₉H₂₅NO₈
Molecular Weight:395.409
Hs Code.:

Synonyms:methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

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Chemical Property of methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

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Technology Process of methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

There total 16 articles about methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate 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: 90.0%

: 1289557-70-5
C₁₈H₂₃NO₈

: 74-88-4
methyl iodide

: 1289557-72-7
methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

: 1289557-60-3
5,6,7-trideoxy-1,2-O-isopropylidene-3-O-triisopropylsilyl-5-isothiocyanato-α-D-gluco-hept-6-enfuranose

: 1289557-72-7
methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

Guidance literature:: Multi-step reaction with 6 steps

1.1: methanol / 6.5 h / 20 °C / Inert atmosphere

2.1: mesitylenecarbonitrile oxide / acetonitrile / 3 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

4.2: 1.5 h / 0 - 20 °C / Inert atmosphere

5.1: sodium periodate; rhodium(III) chloride hydrate; water / tetrachloromethane; acetonitrile / 6 h / 20 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With sodium periodate; rhodium(III) chloride hydrate; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; mesitylenecarbonitrile oxide; In tetrahydrofuran; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

: 1289557-57-8
(E)-5,6,7-trideoxy-1,2-O-isopropylidene-3-O-triisopropylsilyl-7-thiocyanato-α-D-xylo-hept-5-enfuranose

: 1289557-72-7
methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-heptane / 24 h / 90 °C / Inert atmosphere

2.1: methanol / 6.5 h / 20 °C / Inert atmosphere

3.1: mesitylenecarbonitrile oxide / acetonitrile / 3 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

5.2: 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: sodium periodate; rhodium(III) chloride hydrate; water / tetrachloromethane; acetonitrile / 6 h / 20 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With sodium periodate; rhodium(III) chloride hydrate; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; mesitylenecarbonitrile oxide; In tetrahydrofuran; methanol; tetrachloromethane; n-heptane; N,N-dimethyl-formamide; acetonitrile; 1.1: aza-Claisen rearrangement;
DOI:10.1016/j.tetasy.2011.02.004