((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate

Base Information

• Chemical Name: ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate
• CAS No.: 1450890-99-9
• Molecular Formula: C₁₇H₁₉NO₈
• Molecular Weight: 365.34
• Mol file: 1450890-99-9.mol

Synonyms:((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate

Chemical Property of ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate

There total 4 articles about ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate 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: 79.0%

C10H13NO7 + benzyl alcohol (100-51-6,185532-71-2) → ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate (1450890-99-9)

Guidance literature:

With potassium carbonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In toluene; at 20 ℃; for 24h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/cctc.202100795

Reference yield: 68.0%

3,4,6-tri-O-acetyl-1,2-dideoxy-2-nitro-galactal (19128-75-7) + benzyl alcohol (100-51-6,185532-71-2) → ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate (1450890-99-9)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo401165y

Reference yield:

triacetyl-D-galactal (4098-06-0) → ((2R,3R,6S)-3-acetoxy-6-(benzyloxy)-5-nitro-3,6-dihydro-2Hpyran-2-yl)methyl acetate (1450890-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutylammonium nitrate / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 0.25 h / Inert atmosphere

3: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; tetrabutylammonium nitrate; triethylamine; In dichloromethane; 3: |Ferrier Carbohydrate Rearrangement;

DOI:10.1021/jo401165y

upstream raw materials:

3,4,6-tri-O-acetyl-1,2-dideoxy-2-nitro-galactal

benzyl alcohol

triacetyl-D-galactal

Trifluoro-acetic acid (4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-nitro-tetrahydro-pyran-2-yl ester