2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate

Base Information

• Chemical Name: 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate
• CAS No.: 354567-46-7
• Molecular Formula: C₅₉H₁₀₀NO₁₂P
• Molecular Weight: 1046.42
• Mol file: 354567-46-7.mol

Synonyms:2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate

Chemical Property of 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate

There total 16 articles about 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate 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: 58.0%

diphenylmethyl 2,6-anhydro-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-D-glycero-D-ido-heptonate (354567-45-6) → 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate (354567-46-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1016/S0008-6215(01)00055-6

Reference yield:

Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (99519-05-8) → 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate (354567-46-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / DMAP; TfN₃ / methanol; CH₂Cl₂ / 18 h / 20 °C

2.1: 74 percent / NaH / dimethylformamide / 20 h / 20 °C

3.1: [C₈H₁₂Ir(PMePh₂)2]PF₆; H₂ / tetrahydrofuran / 3 h / 20 °C

3.2: 65 percent / I₂; water; pyridine / 12 h / 20 °C

4.1: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

5.1: 93 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

6.1: PPh₃; NH₃ / tetrahydrofuran; H₂O / 24 h / 60 °C

7.1: 74 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 20 °C

8.1: HCl; water / dioxane / 3 h / 60 °C

8.2: 26 percent / dimethylformamide / 1 h / 60 °C

9.1: 62 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

10.1: 80 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

11.1: 80 percent / HCl; water / tetrahydrofuran / 6 h / 20 °C

12.1: 58 percent / H₂ / Pd(OH)2/C / ethanol / 16 h / 20 °C

With hydrogenchloride; dmap; [C₈H₁₂Ir(PMePh₂)2]PF₆; triflic azide; ammonia; water; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00055-6

Reference yield:

(R)-1,3-dihydroxytetradecane (139623-13-5) → 2,6-anhydro-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-4-O-[(R)-3-hydroxytetradecyl]-D-glycero-D-ido-heptonate (354567-46-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 97 percent / pTsOH*H₂O / dimethylformamide / 1 h / 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / 0 °C

3.1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 74 percent / NaH / dimethylformamide / 20 h / 20 °C

5.1: [C₈H₁₂Ir(PMePh₂)2]PF₆; H₂ / tetrahydrofuran / 3 h / 20 °C

5.2: 65 percent / I₂; water; pyridine / 12 h / 20 °C

6.1: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

7.1: 93 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

8.1: PPh₃; NH₃ / tetrahydrofuran; H₂O / 24 h / 60 °C

9.1: 74 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 20 °C

10.1: HCl; water / dioxane / 3 h / 60 °C

10.2: 26 percent / dimethylformamide / 1 h / 60 °C

11.1: 62 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

12.1: 80 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

13.1: 80 percent / HCl; water / tetrahydrofuran / 6 h / 20 °C

14.1: 58 percent / H₂ / Pd(OH)2/C / ethanol / 16 h / 20 °C

With hydrogenchloride; dmap; [C₈H₁₂Ir(PMePh₂)2]PF₆; ammonia; water; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00055-6

upstream raw materials:

diphenylmethyl 2,6-anhydro-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5-O-diphenylphosphono-3-[(R)-3-(dodecyloxy)tetradecanamido]-D-glycero-D-ido-heptonate

(R)-1,3-dihydroxytetradecane

Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

(R)-3-benzyloxy-1-hydroxytetradecane

Refernces