allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Base Information

Chemical Name:allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside
CAS No.:288403-14-5
Molecular Formula:C₄₄H₆₉Cl₃NO₁₁PSi
Molecular Weight:953.45
Hs Code.:

allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Synonyms:allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

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Chemical Property of allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

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Technology Process of allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

There total 10 articles about allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)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: 91.0%

: 288403-13-4
allyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

: 288403-14-5
allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0008-6215(01)00134-3

Reference yield:

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

: 288403-14-5
allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 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

With dmap; sodium hydroxide; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 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

: 288403-14-5
allyl 6-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-(diphenylphosphono)-3-O-[(R)-3-(hydroxy)tetradecyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 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

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