3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose

Base Information

• Chemical Name: 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose
• CAS No.: 848415-04-3
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37
• Mol file: 848415-04-3.mol

Synonyms:3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose

Chemical Property of 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose

There total 1 articles about 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose 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: 72.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose (848415-04-3) + 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(E)-enfuranos-7-ulose (848415-03-2)

Guidance literature:

In chloroform; at 20 ℃; for 5h;

DOI:10.1002/jhet.5570410605

Reference yield: 67.0%

trimethylsulfoxonium iodide (1774-47-6) + 3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose (848415-04-3) → 3-O-benzyl-5,6-C-methylene-5,6,8-trideoxy-1,2-O-isopropylidene-D-glycero-β-L-iodo-octos-7-ulofuranose (918165-25-0)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 10 ℃; for 0.5h;

DOI:10.1016/j.tetasy.2006.09.025

Reference yield:

3-O-benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-D-xylo-oct-5-(Z)-enfuranos-7-ulose (848415-04-3) → 3-O-benzyl-5,6,7,9-tetradeoxy-1,2-O-isopropylidene-α-D-xylo-nonos-8-ulofuranose

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / NaH / dimethylsulfoxide / 0.5 h / 10 °C

2: 82 percent / tri-n-butyltin hydride; AIBN / benzene / 3 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In dimethyl sulfoxide; benzene;

DOI:10.1016/j.tetasy.2006.09.025

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

1-triphenylphosphoranylidene-2-propanone

Downstream raw materials:

3-O-benzyl-5,6-C-methylene-5,6,8-trideoxy-1,2-O-isopropylidene-D-glycero-β-L-iodo-octos-7-ulofuranose

(3R,4S,5R)-4-Methyl-5-((S)-1-methyl-butyl)-tetrahydro-furan-2,3-diol