methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate

Base Information

• Chemical Name: methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate
• CAS No.: 1350467-77-4
• Molecular Formula: C₁₇H₁₆BrCl₃O₈
• Molecular Weight: 535.564

Synonyms:methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate

Chemical Property of methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate

Chemical Property:

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Technology Process of methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate

There total 6 articles about methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate 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: 65.0%

C17H15(2)H2Cl3O8 (1350467-76-3) → methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{2H}-β-D-glucopyranosid)uronate (1350467-77-4)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 5h; Reflux;

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) → methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{2H}-β-D-glucopyranosid)uronate (1350467-77-4)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ja209067v

Reference yield:

methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate (52173-67-8) → methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{2H}-β-D-glucopyranosid)uronate (1350467-77-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

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

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

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

Downstream raw materials:

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

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

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