allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside
• CAS No.: 288402-99-3
• Molecular Formula: C₃₆H₅₆F₃NO₈
• Molecular Weight: 687.838

Synonyms:allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside

Chemical Property of allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside

Chemical Property:

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Technology Process of allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside

There total 5 articles about allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-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: 84.0%

(R)-1-methanesulfonyloxy-3-(4-methoxybenzyloxy)tetradecane (288402-98-2) + 1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside (139629-59-7) → allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside (288402-99-3)

Guidance literature:

1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

(R)-1-methanesulfonyloxy-3-(4-methoxybenzyloxy)tetradecane; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/S0008-6215(01)00134-3

Reference yield:

2-(4-methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane (288402-96-0) → allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside (288402-99-3)

Guidance literature:

Multi-step reaction with 3 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

With sodium hydride; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00134-3

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → allyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-(4-methoxybenzyloxy)tetradecyl]-2-trifluoroacetamide-α-D-glucopyranoside (288402-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 20 °C

2.1: 93 percent / DIBAL / CH₂Cl₂ / 2 h / 0 °C

3.1: 99 percent / Et₃N / 1 h / 0 °C

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

4.2: 84 percent / dimethylformamide / 18 h / 20 °C

With sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00134-3

upstream raw materials:

(R)-1-methanesulfonyloxy-3-(4-methoxybenzyloxy)tetradecane

1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside

2-(4-methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

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

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

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

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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