(4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside

Base Information

• Chemical Name: (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside
• CAS No.: 1450891-02-7
• Molecular Formula: C₁₈H₂₁NO₉
• Molecular Weight: 395.366
• Mol file: 1450891-02-7.mol

Synonyms:(4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside

Chemical Property of (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside

There total 3 articles about (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside 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: 84.0%

3,4,6-tri-O-acetyl-1,2-dideoxy-2-nitro-galactal (19128-75-7) + 4-Methoxybenzyl alcohol (105-13-5) → (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside (1450891-02-7)

Guidance literature:

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

DOI:10.1021/jo401165y

Reference yield:

triacetyl-D-galactal (4098-06-0) → (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside (1450891-02-7)

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

Reference yield:

Trifluoro-acetic acid (4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-nitro-tetrahydro-pyran-2-yl ester (102633-91-0,102633-92-1,102633-93-2,102633-94-3,102633-95-4,102633-96-5,102633-97-6,102633-98-7,102633-99-8,102634-00-4,102634-01-5,102634-02-6) → (4′-methoxyphenyl)methyl 4,6-di-O-acetyl-2,3-dideoxy-2-nitro-α-D-threo-hex-2-enopyranoside (1450891-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0.25 h / Inert atmosphere

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

With dmap; triethylamine; In dichloromethane; 2: |Ferrier Carbohydrate Rearrangement;

DOI:10.1021/jo401165y

upstream raw materials:

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

4-Methoxybenzyl alcohol

triacetyl-D-galactal

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