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

Base Information

• Chemical Name: diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate
• CAS No.: 338951-71-6
• Molecular Formula: C₆₇H₁₀₇NO₉
• Molecular Weight: 1070.59

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

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

Chemical Property:

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

There total 9 articles about diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-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: 50.0%

diazodiphenylmethane (908093-98-1) + 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile (338951-70-5) → diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate (338951-71-6)

Guidance literature:

2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile; With hydrogenchloride; water; In 1,4-dioxane; at 60 ℃; for 3h;

diazodiphenylmethane; In N,N-dimethyl-formamide; at 60 ℃; for 1h;

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

Reference yield:

(4R)-3-dodecyloxy-1-hydroxytetradecane (354567-16-1) → diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate (338951-71-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 73 percent / NaH / dimethylformamide / 20 h / 20 °C

3.1: 70 percent / SeO₂; AcOH / dioxane / 1 h / Heating

4.1: 91 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

5.1: 75 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

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

7.1: 79 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

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

8.2: 50 percent / dimethylformamide / 1 h / 60 °C

With hydrogenchloride; dmap; selenium(IV) oxide; ammonia; water; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

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

Reference yield:

(4R)-2,4-diundexyl-1,3-dioxane (354567-15-0) → diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate (338951-71-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 89 percent / DIBAL / CH₂Cl₂ / 5 h / 20 °C

2.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 73 percent / NaH / dimethylformamide / 20 h / 20 °C

4.1: 70 percent / SeO₂; AcOH / dioxane / 1 h / Heating

5.1: 91 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

6.1: 75 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

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

8.1: 79 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

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

9.2: 50 percent / dimethylformamide / 1 h / 60 °C

With hydrogenchloride; dmap; selenium(IV) oxide; ammonia; water; sodium hydride; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

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

upstream raw materials:

diazodiphenylmethane

2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

(4R)-2,4-diundexyl-1,3-dioxane

(4R)-3-dodecyloxy-1-hydroxytetradecane

Downstream raw materials:

diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

2,6-anhydro-3-deoxy-5-O-diphenylphosphono-4-O-[(R)-3-(dodecyloxy)tetradecyl]-3-[(R)-3-hydroxytetradecanamido]-7-O-methyl-D-glycero-D-ido-heptonate

2,6-anhydro-3-deoxy-5-O-diphenylphosphono-4-O-[(dodecyloxy)tetradecyl]-3-[(R)-3-hydroxytetradecanamido]-D-glycero-D-ido-heptonic acid

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

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