2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

Base Information

• Chemical Name: 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid
• CAS No.: 1350467-70-7
• Molecular Formula: C₁₂H₉Cl₃O₆
• Molecular Weight: 356.551
• Mol file: 1350467-70-7.mol

Synonyms:2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

Chemical Property of 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

There total 8 articles about 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid 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: 54.0%

methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosid)uronate (1350467-78-5) → 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid (1350467-70-7)

Guidance literature:

methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosid)uronate; With sodium hydroxide; In acetone; at 0 ℃; for 0.0833333h;

With hydrogenchloride; In water; acetone;

DOI:10.1021/ja209067v

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid (1350467-70-7)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogen bromide; acetic anhydride / dichloromethane; acetic acid / 0 - 4 °C

2: silver(l) oxide / acetonitrile / 20 °C / Darkness

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

4: palladium 10% on activated carbon; deuterium / ethyl acetate

5: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 5 h / Reflux

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

7: sodium hydroxide / acetone / 0.08 h / 0 °C

With N-Bromosuccinimide; palladium 10% on activated carbon; hydrogen bromide; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; deuterium; sodium hydroxide; silver(l) oxide; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; acetic acid; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/ja209067v

Reference yield:

methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate (1350467-75-2) → 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid (1350467-70-7)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; deuterium / ethyl acetate

2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 5 h / Reflux

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

4: sodium hydroxide / acetone / 0.08 h / 0 °C

With N-Bromosuccinimide; palladium 10% on activated carbon; 1,8-diazabicyclo[5.4.0]undec-7-ene; deuterium; sodium hydroxide; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/ja209067v

upstream raw materials:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate

methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate

C₁₇H₁₅⁽²⁾H₂Cl₃O₈

Refernces