allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Base Information

Chemical Name:allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside
CAS No.:288403-23-6
Molecular Formula:C₅₂H₈₀Cl₃FNO₁₁P
Molecular Weight:1051.54
Hs Code.:

allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Synonyms:allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

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Chemical Property of allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

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Technology Process of allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

There total 14 articles about allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside 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: 80.0%

: 288403-16-7
allyl 2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

: 288403-23-6
allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: With diethylamino-sulfur trifluoride; In 1,2-dimethoxyethane; at 0 ℃; for 3h;
DOI:10.1016/S0008-6215(01)00134-3

Reference yield:

: 288402-98-2
(R)-1-methanesulfonyloxy-3-(4-methoxybenzyloxy)tetradecane

: 288403-23-6
allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH (in oil)77 / dimethylformamide / 0.25 h / 0 °C

1.2: 84 percent / dimethylformamide / 18 h / 20 °C

2.1: 99 percent / aq. NaOH / ethanol

3.1: 94 percent / 0.5 h / 20 °C

4.1: 83 percent / 80 percent AcOH / H₂O / 1 h / 60 °C

5.1: 96 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

6.1: 98 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

7.1: 91 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C

8.1: 95 percent / Et₃N; DMAP / tetrahydrofuran / 24 h / 20 °C

9.1: 91 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

10.1: 80 percent / diethylaminosulfur trifluoride / 1,2-dimethoxy-ethane / 3 h / 0 °C

With hydrogenchloride; dmap; sodium hydroxide; diethylamino-sulfur trifluoride; sodium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00134-3

Reference yield:

: 288402-96-0
2-(4-methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane

: 288403-23-6
allyl 2,6-dideoxy-4-O-(diphenylphosphono)-6-fluoro-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1.1: 93 percent / DIBAL / CH₂Cl₂ / 2 h / 0 °C

2.1: 99 percent / Et₃N / 1 h / 0 °C

3.1: NaH (in oil)77 / dimethylformamide / 0.25 h / 0 °C

3.2: 84 percent / dimethylformamide / 18 h / 20 °C

4.1: 99 percent / aq. NaOH / ethanol

5.1: 94 percent / 0.5 h / 20 °C

6.1: 83 percent / 80 percent AcOH / H₂O / 1 h / 60 °C

7.1: 96 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

8.1: 98 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

9.1: 91 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C

10.1: 95 percent / Et₃N; DMAP / tetrahydrofuran / 24 h / 20 °C

11.1: 91 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

12.1: 80 percent / diethylaminosulfur trifluoride / 1,2-dimethoxy-ethane / 3 h / 0 °C

With hydrogenchloride; dmap; sodium hydroxide; diethylamino-sulfur trifluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00134-3