(+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate
• CAS No.: 393818-85-4
• Molecular Formula: C₂₃H₂₇Cl₂NO₆S
• Molecular Weight: 516.442

Synonyms:(+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate

Chemical Property of (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate

There total 7 articles about (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate 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: 96.0%

p-toluenesulfonyl chloride (98-59-9) + (+)-2-(3,4-dichlorophenyl)-N-{2-[(2R,3S,6S)-3-hydroxy-6-methoxyoxan-2-yl]ethyl}acetamide (393818-84-3) → (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate (393818-85-4)

Guidance literature:

With dmap; triethylamine; In chloroform; for 1h; Heating;

DOI:10.1002/1521-4184(200109)334:8/9<284::AID-ARDP284>3.0.CO;2-B

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate (393818-85-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 75 percent / PPh₃; CHI₃; imidazole / toluene / 2.25 h / Heating

2.1: 96 percent / H₂; NaOH / Raney Ni / H₂O; methanol / 24 h / 40 °C / 3975.32 Torr

3.1: 62 percent / N-bromosuccinimide; BaCO₃; AIBN / CCl₄ / 0.5 h / Heating

4.1: 91 percent / dimethylsulfoxide / 1 h / 70 °C

5.1: aq. NaOH / methanol / 0.17 h / 20 °C

5.2: H₂; aq. NaOH / Raney Ni / methanol / 14 h / 20 °C / 3975.32 Torr

6.1: 254 mg / CH₂Cl₂; H₂O; methanol / 0.5 h / 20 °C

7.1: 96 percent / 4-dimethylaminopyridine; Et₃N / CHCl₃ / 1 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; N-Bromosuccinimide; iodoform; 2,2'-azobis(isobutyronitrile); hydrogen; triethylamine; triphenylphosphine; barium carbonate; nickel; In methanol; tetrachloromethane; dichloromethane; chloroform; water; dimethyl sulfoxide; toluene;

DOI:10.1002/1521-4184(200109)334:8/9<284::AID-ARDP284>3.0.CO;2-B

Reference yield:

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine (65530-27-0) → (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate (393818-85-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / H₂; NaOH / Raney Ni / H₂O; methanol / 24 h / 40 °C / 3975.32 Torr

2.1: 62 percent / N-bromosuccinimide; BaCO₃; AIBN / CCl₄ / 0.5 h / Heating

3.1: 91 percent / dimethylsulfoxide / 1 h / 70 °C

4.1: aq. NaOH / methanol / 0.17 h / 20 °C

4.2: H₂; aq. NaOH / Raney Ni / methanol / 14 h / 20 °C / 3975.32 Torr

5.1: 254 mg / CH₂Cl₂; H₂O; methanol / 0.5 h / 20 °C

6.1: 96 percent / 4-dimethylaminopyridine; Et₃N / CHCl₃ / 1 h / Heating

With dmap; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); hydrogen; triethylamine; barium carbonate; nickel; In methanol; tetrachloromethane; dichloromethane; chloroform; water; dimethyl sulfoxide;

DOI:10.1002/1521-4184(200109)334:8/9<284::AID-ARDP284>3.0.CO;2-B

upstream raw materials:

p-toluenesulfonyl chloride

(+)-2-(3,4-dichlorophenyl)-N-{2-[(2R,3S,6S)-3-hydroxy-6-methoxyoxan-2-yl]ethyl}acetamide

methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-erythrohexopyranoside

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

Downstream raw materials:

(+)-1-[(1R,5R,6R)-6-azido-9-oxa-2-azabicyclo[3.3.1]nonan-2-yl]-2-(3,4-dichlorophenyl)ethan-1-one

(+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide

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