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

Base Information

• Chemical Name: 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-3-[(R)-3-(dodecyloxy)tetradecanamido]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile
• CAS No.: 354567-27-4
• Molecular Formula: C₅₇H₁₀₀N₂O₇
• Molecular Weight: 925.43

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-3-[(R)-3-(dodecyloxy)tetradecanamido]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

There total 12 articles about 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-3-[(R)-3-(dodecyloxy)tetradecanamido]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile 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: 74.0%

(R)-3-(dodecanoyloxy)tetradecanoic acid (338952-12-8) + (4aR,6S,7S,8R,8aS)-7-Amino-8-((R)-3-benzyloxy-tetradecyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbonitrile (288402-93-7) → 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-3-[(R)-3-(dodecyloxy)tetradecanamido]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile (354567-27-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

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

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-3-[(R)-3-(dodecyloxy)tetradecanamido]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile (354567-27-4)

Guidance literature:

Multi-step reaction with 9 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

With dmap; [C₈H₁₂Ir(PMePh₂)2]PF₆; ammonia; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; 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-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-3-[(R)-3-(dodecyloxy)tetradecanamido]-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile (354567-27-4)

Guidance literature:

Multi-step reaction with 9 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

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

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

upstream raw materials:

(R)-3-(dodecanoyloxy)tetradecanoic acid

(4aR,6S,7S,8R,8aS)-7-Amino-8-((R)-3-benzyloxy-tetradecyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbonitrile

benzaldehyde dimethyl acetal

(R)-1,3-dihydroxytetradecane

Downstream raw materials:

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

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

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

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

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