6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose

Base Information

• Chemical Name: 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose
• CAS No.: 110089-65-1
• Molecular Formula: C₁₈H₂₄O₉S
• Molecular Weight: 416.449
• Mol file: 110089-65-1.mol

Synonyms:

Chemical Property of 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose

There total 9 articles about 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose 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: 68.0%

3-O-acetyl-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose (110089-62-8) → 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose (110089-65-1) + 3-O-acetyl-5,6-anhydro-1,2-O-isopropylidene-β-L-talofuranose (110089-64-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 16h;

DOI:10.1007/BF00810877

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate (10578-85-5) → 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose (110089-65-1)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄

2: 92 percent / pyridine / 12 h / Ambient temperature

3: 94 percent / acetic acid/water (3:1) / 24 h / Ambient temperature

4: 60 percent / imidazole/molecular sieves 4 Angstroem / dimethylformamide / 16 h / 4 °C

5: 60 percent / pyridine / 48 h / 35 °C

6: 23 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h

With 1H-imidazole; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; acetic acid; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1007/BF00810877

Reference yield:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose (26775-14-4) → 6-O-acetyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose (110089-65-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / acetic acid/water (3:1) / 24 h / Ambient temperature

2: 60 percent / imidazole/molecular sieves 4 Angstroem / dimethylformamide / 16 h / 4 °C

3: 60 percent / pyridine / 48 h / 35 °C

4: 23 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h

With 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; acetic acid; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1007/BF00810877

upstream raw materials:

6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose

p-toluenesulfonyl chloride

3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-α-D-glucofuranose

Refernces