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

Base Information

• Chemical Name: methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate
• CAS No.: 1289557-78-3
• Molecular Formula: C₂₀H₂₅NO₁₀
• Molecular Weight: 439.419
• Mol file: 1289557-78-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-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 + acetic anhydride (108-24-7) → methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate (1289557-76-1) + methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate (1289557-78-3)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose (1289557-68-1) → methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate (1289557-76-1) + methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate (1289557-78-3)

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:

(E)-3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-7-thiocyanato-α-D-xylo-hept-5-enfuranose (1289557-56-7) → methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate (1289557-76-1) + methyl 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-(methoxycarbonylamino)-β-D-gluco-hexofuranuronate (1289557-78-3)

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

upstream raw materials:

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

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

3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose

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