phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

Base Information

Chemical Name:phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside
CAS No.:1342295-21-9
Molecular Formula:C₂₇H₃₃Cl₇N₂O₉S
Molecular Weight:809.804
Hs Code.:

phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

Synonyms:phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

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Chemical Property of phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

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Technology Process of phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

There total 10 articles about phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside 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: 99.0%

: 1342295-18-4
phenyl 2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

: 79-04-9
chloroacetyl chloride

: 1342295-21-9
phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 19h; Inert atmosphere;
DOI:10.1021/ol202639v

Reference yield:

: 1342295-08-2
phenyl 2-azido-2-deoxy-1-thio-α-D-xylopyranoside

: 1342295-21-9
phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 0 - 35 °C / Inert atmosphere

2.1: trimethylphosphane / dichloromethane; toluene / 0.75 h / Molecular sieve; Inert atmosphere

2.2: 5 h / 20 °C / Inert atmosphere

2.3: 1 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

5.1: diethyl ether / 0.08 h / 20 °C / Molecular sieve

5.2: 0.67 h / -40 °C

6.1: pyridine / dichloromethane / 19 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; acetic acid; trimethylphosphane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol202639v

Reference yield:

: phenyl 3,4-di-O-acetyl-2-azido-2-deoxy-1-thio-D-xylopyranoside

: 1342295-21-9
phenyl 3-O-chloroacetyl-2-deoxy-4-O-(4'-N'-monodemethyl-N'-trichloroethoxycarbamoyl-β-D-forosaminyl)-2-N-methyl-N-trichloroethoxycarbamoyl-1-thio-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: methanol; sodium methylate / 0 - 20 °C

2.1: 1H-imidazole / dichloromethane / 0 - 35 °C / Inert atmosphere

3.1: trimethylphosphane / dichloromethane; toluene / 0.75 h / Molecular sieve; Inert atmosphere

3.2: 5 h / 20 °C / Inert atmosphere

3.3: 1 h / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6.1: diethyl ether / 0.08 h / 20 °C / Molecular sieve

6.2: 0.67 h / -40 °C

7.1: pyridine / dichloromethane / 19 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; methanol; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; trimethylphosphane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol202639v