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

Base Information

• Chemical Name: (+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide
• CAS No.: 393818-86-5
• Molecular Formula: C₁₆H₂₀Cl₂N₄O₃
• Molecular Weight: 387.266

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 8 articles about (+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide 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: 81.0%

(+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate (393818-85-4) → (+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide (393818-86-5)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 2.5h; 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) → (+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide (393818-86-5)

Guidance literature:

Multi-step reaction with 8 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

8.1: 81 percent / NaN₃ / dimethylsulfoxide / 2.5 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; N-Bromosuccinimide; sodium azide; 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) → (+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide (393818-86-5)

Guidance literature:

Multi-step reaction with 7 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

7.1: 81 percent / NaN₃ / dimethylsulfoxide / 2.5 h / Heating

With dmap; sodium hydroxide; N-Bromosuccinimide; sodium azide; 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:

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

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

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[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

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