5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose

Base Information

• Chemical Name: 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose
• CAS No.: 608525-47-9
• Molecular Formula: C₂₀H₂₇NO₁₂S
• Molecular Weight: 505.5
• Mol file: 608525-47-9.mol

Synonyms:5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose

Chemical Property of 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose

There total 4 articles about 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-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: 59.0%

3-(ethoxycarbonyl)(nitro)methyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose (608525-46-8) → 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose (608525-47-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1016/S0040-4020(03)00988-8

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose (608525-47-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 26 percent / AcONH₄ / dimethylformamide / 40 h / 20 °C

2: AcOH / methanol; H₂O / 22 h / 20 °C

3: 0.407 g / pyridine / 10 h / -20 °C

4: 59 percent / Bu₄NF / tetrahydrofuran / 7 h / 20 °C

With ammonium acetate; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)00988-8

Reference yield:

[(3aR,5R,6R,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-nitro-acetic acid ethyl ester → 5-O-ethoxycarbonyl-1,2-O-isopropylidene-3-nitromethyl-6-O-p-toluenesulfonyl-α-D-allofuranose (608525-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.407 g / pyridine / 10 h / -20 °C

2: 59 percent / Bu₄NF / tetrahydrofuran / 7 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine;

DOI:10.1016/S0040-4020(03)00988-8

upstream raw materials:

3-(ethoxycarbonyl)(nitro)methyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

(3-ethoxycarbonyl)(nitro)methyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose