Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester

Base Information

• Chemical Name: Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester
• CAS No.: 187726-68-7
• Molecular Formula: C₇₉H₁₃₀N₄O₁₄P₂
• Molecular Weight: 1421.87
• Mol file: 187726-68-7.mol

Synonyms:

Chemical Property of Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester

There total 18 articles about Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester 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: 56.0%

C32H56ClO4P (150712-00-8) + Dodecanoic acid (R)-1-{[(2S,3R,4R,5S,6R)-6-azidomethyl-5-(bis-benzyloxy-phosphoryloxy)-4-hydroxy-2-methoxy-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester (150712-08-6) → Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester (187726-68-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)93372-0

Reference yield:

lauric acid (143-07-7) → Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester (187726-68-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / DCC, DMAP / CH₂Cl₂

2: 82 percent / TMSI / CH₂Cl₂

3: 64 percent / CCl₃CN, pyridine / CHCl₃

4: PCl₅ / CHCl₃

5: 56 percent / DMAP, Et₃N / CH₂Cl₂

With pyridine; dmap; trimethylsilyl iodide; phosphorus pentachloride; triethylamine; trichloroacetonitrile; dicyclohexyl-carbodiimide; In dichloromethane; chloroform;

DOI:10.1016/S0040-4039(00)93372-0

Reference yield:

methyl n-dodecanoate (111-82-0) → Dodecanoic acid 1-{[(2R,3R,4R,5R,6S)-2-azidomethyl-3-(bis-benzyloxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-methoxy-tetrahydro-pyran-4-yloxy]-benzyloxy-phosphorylmethyl}-dodecyl ester (187726-68-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 64 percent / n-butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / NaBH₄ / methanol

3: 82 percent / DCC, DMAP / CH₂Cl₂

4: 82 percent / TMSI / CH₂Cl₂

5: 64 percent / CCl₃CN, pyridine / CHCl₃

6: PCl₅ / CHCl₃

7: 56 percent / DMAP, Et₃N / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; trimethylsilyl iodide; phosphorus pentachloride; triethylamine; trichloroacetonitrile; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1016/S0040-4039(00)93372-0

upstream raw materials:

C₃₂H₅₆ClO₄P

Dodecanoic acid (R)-1-{[(2S,3R,4R,5S,6R)-6-azidomethyl-5-(bis-benzyloxy-phosphoryloxy)-4-hydroxy-2-methoxy-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester

lauric acid

methyl n-dodecanoate