3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose

Base Information

• Chemical Name: 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose
• CAS No.: 98855-09-5
• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.51
• Mol file: 98855-09-5.mol

Synonyms:3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose

Chemical Property of 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose

There total 7 articles about 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose 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: 82.0%

3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-β-L-arabino-hex-5-enofuranose (65434-50-6) → 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose (98855-09-5)

Guidance literature:

With hydrogen; nickel; In ethanol; under 2585.7 Torr;

DOI:10.1021/jo00224a025

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose (65462-15-9) → 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose (98855-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) DME, 0.5 h, 2.) DME, RT, 1.5 h

2: 82 percent / H₂ / Raney Ni / ethanol / 2585.7 Torr

With n-butyllithium; hydrogen; nickel; In ethanol;

DOI:10.1021/jo00224a025

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-galactofuranose (10368-86-2) → 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose (98855-09-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / NaH / dimethylformamide / 24 h

2: 80 percent / aq. AcOH / 24 h / Ambient temperature

3: aq. sodium metaperiodate / dioxane / 4 h

4: 1.) n-BuLi / 1.) DME, 0.5 h, 2.) DME, RT, 1.5 h

5: 82 percent / H₂ / Raney Ni / ethanol / 2585.7 Torr

With sodium periodate; n-butyllithium; hydrogen; sodium hydride; acetic acid; nickel; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00224a025

upstream raw materials:

3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-β-L-arabino-hex-5-enofuranose

3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose

1,2:5,6-di-O-isopropylidene-α-D-galactofuranose

3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose