5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone

Base Information

• Chemical Name: 5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone
• CAS No.: 144363-73-5
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 144363-73-5.mol

Synonyms:5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone

Chemical Property of 5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone

There total 1 articles about 5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone 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: 71.0%

2,6-O-isopropylidene-α-D-glucoisosaccharino-1,4-lactone (78687-63-5) + benzyl bromide (100-39-0) → 5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone (144363-73-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 18h;

DOI:10.1055/s-1992-26224

Reference yield: 53.0%

5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone (144363-73-5) → 5-O-Benzyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentofuranose (144363-74-6,144409-25-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1055/s-1992-26224

Reference yield:

5-O-Benzyl-2-C-hydroxymethyl-2,2'-O-isopropylidene-α-D-isosaccharino-1,4-lactone (144363-73-5) → (3S,5S)-5-Benzyloxymethyl-3-hydroxymethyl-tetrahydro-furan-2,3-diol

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C

2: aq.HOAc / 3 h / 80 °C

With diisobutylaluminium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1055/s-1992-26224

upstream raw materials:

2,6-O-isopropylidene-α-D-glucoisosaccharino-1,4-lactone

benzyl bromide

Downstream raw materials:

5-O-Benzyl-3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-erythro-pentofuranose

2-C-Acetoxymethyl-1,2-di-O-acetyl-5-O-benzyl-3-deoxy-D-ribofuranose

9-(2-Acetoxymethyl-2-O-acetyl-5-O-benzyl-D-erythro-pentofuranosyl)-6-chloro-9H-purine