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

Base Information

• Chemical Name: 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose
• CAS No.: 1289557-66-9
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411
• Mol file: 1289557-66-9.mol

Synonyms:3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose

Chemical Property of 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose

There total 14 articles about 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose 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: 92.0%

3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxythiocarbonylamino)-α-D-gluco-hept-6-enfuranose (1289557-62-5) → 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose (1289557-66-9)

Guidance literature:

With mesitylenecarbonitrile oxide; In acetonitrile; at 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.004

Reference yield: 77.0%

5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose (1289557-68-1) + benzyl bromide (100-39-0) → 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose (1289557-66-9)

Guidance literature:

5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose (1289557-58-9) → 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose (1289557-66-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With mesitylenecarbonitrile oxide; In methanol; acetonitrile;

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

Downstream raw materials:

C₁₈H₂₃NO₈

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

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

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