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

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Chemical Name:methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate
CAS No.:1289557-76-1
Molecular Formula:C₂₀H₂₅NO₁₀
Molecular Weight:439.419
Hs Code.:

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

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

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

There total 18 articles about methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-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: 38.0%

: C₁₆H₂₁NO₈

: 108-24-7
acetic anhydride

: 1289557-76-1
methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

: 1289557-78-3
methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate

Guidance literature:: With pyridine; dmap; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

: 1289557-68-1
5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose

: 1289557-76-1
methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

: 1289557-78-3
methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 1.5 h / 0 - 20 °C / Inert atmosphere

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

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

4.1: Amberlite IR-120 (H⁺) / 1,4-dioxane; water / 18.5 h / 65 °C

5.1: pyridine; dmap / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium periodate; rhodium(III) chloride hydrate; water; sodium hydride; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

: 1289557-56-7
(E)-3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-7-thiocyanato-α-D-xylo-hept-5-enfuranose

: 1289557-76-1
methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate

: 1289557-78-3
methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate

Guidance literature:: Multi-step reaction with 7 steps

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

2: methanol / 2.67 h / 0 - 20 °C / Inert atmosphere

3: mesitylenecarbonitrile oxide / acetonitrile / 3.5 h / 20 °C / Inert atmosphere

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

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

6: Amberlite IR-120 (H⁺) / 1,4-dioxane; water / 18.5 h / 65 °C

7: pyridine; dmap / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium periodate; rhodium(III) chloride hydrate; water; potassium carbonate; mesitylenecarbonitrile oxide; In 1,4-dioxane; methanol; tetrachloromethane; n-heptane; water; N,N-dimethyl-formamide; acetonitrile; 1: aza-Claisen rearrangement;
DOI:10.1016/j.tetasy.2011.02.004