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
Hs Code.:

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

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

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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%

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

: 1350467-70-7
2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

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:

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

: 1350467-70-7
2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

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:

: 1350467-75-2
methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate

: 1350467-70-7
2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid

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