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

Base Information

• Chemical Name: 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose
• CAS No.: 1289557-58-9
• Molecular Formula: C₁₈H₂₁NO₄S
• Molecular Weight: 347.435
• Mol file: 1289557-58-9.mol

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

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

There total 4 articles about 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-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: 53.0%

(E)-3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-7-thiocyanato-α-D-xylo-hept-5-enfuranose (1289557-56-7) → 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose (1289557-59-0) + 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose (1289557-58-9)

Guidance literature:

In n-heptane; at 90 ℃; for 24h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-63-4) → 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose (1289557-59-0) + 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose (1289557-58-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 1.75 h / 0 - 20 °C / Inert atmosphere

2: acetonitrile / 2.5 h / 20 °C / Inert atmosphere

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

With triethylamine; In n-heptane; dichloromethane; acetonitrile; 3: aza-Claisen rearrangement;

DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose (1289557-59-0) + 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose (1289557-58-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.83 h / -13 °C / Inert atmosphere

1.2: -13 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1.75 h / 0 - 20 °C / Inert atmosphere

3.1: acetonitrile / 2.5 h / 20 °C / Inert atmosphere

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

With diisobutylaluminium hydride; triethylamine; In n-heptane; dichloromethane; toluene; acetonitrile; 4.1: 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)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Downstream raw materials:

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

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