Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester

Base Information

• Chemical Name: Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester
• CAS No.: 134039-26-2
• Molecular Formula: C₈₅H₁₁₉O₁₃P
• Molecular Weight: 1379.85

Synonyms:Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester

Chemical Property of Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester

Chemical Property:

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Technology Process of Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester

There total 16 articles about Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl 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: 84.0%

((S)-3,4-Dihydroxy-butyl)-phosphonic acid benzyl ester (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester (134039-25-1) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester (134039-26-2)

Guidance literature:

With pyridine; In dichloromethane; at 35 ℃; for 2h;

DOI:10.1016/S0040-4039(00)92129-4

Reference yield:

1,2:4,5-dicyclohexylidene-myo-inositol (34361-60-9,55123-24-5,55123-26-7,62012-78-6,104873-71-4) → Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester (134039-26-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 68 percent / BaO/Ba(OH)2 / dimethylformamide / 72 h / 20 °C

2: 1) NaH

3: HOCH₂CH₂OH / CH₂Cl₂

4: 1) NaH

5: 0.05N HCl / methanol

6: 1) NaH

7: 1,5-cyclooctadiene-bis-IrPF₆, activated with H₂ / 1,2-dichloro-ethane

8: 0.1 HCl / CH₂Cl₂; methanol

9: 43 percent

10: 99 percent / 0.2N NaOH / dioxane; methanol; H₂O

11: dioxane / 0.25 h / 20 °C

12: N-methylimidazole / dioxane / 1 h / 20 °C

13: 1) BuLi / 1) THF, -78 deg C, 2) -40 deg C, 1 h

14: 0.05N HCl / methanol

15: 84 percent / pyridine / CH₂Cl₂ / 2 h / 35 °C

With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; barium dihydroxide; sodium hydroxide; n-butyllithium; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen; sodium hydride; ethylene glycol; barium(II) oxide; In 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92129-4

Reference yield:

benzyl bromide (100-39-0) → Hexadecanoic acid (S)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryl}-1-hexadecanoyloxymethyl-propyl ester (134039-26-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) NaH

2: 0.05N HCl / methanol

3: 1) NaH

4: 1,5-cyclooctadiene-bis-IrPF₆, activated with H₂ / 1,2-dichloro-ethane

5: 0.1 HCl / CH₂Cl₂; methanol

6: 43 percent

7: 99 percent / 0.2N NaOH / dioxane; methanol; H₂O

8: dioxane / 0.25 h / 20 °C

9: N-methylimidazole / dioxane / 1 h / 20 °C

10: 1) BuLi / 1) THF, -78 deg C, 2) -40 deg C, 1 h

11: 0.05N HCl / methanol

12: 84 percent / pyridine / CH₂Cl₂ / 2 h / 35 °C

With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium hydroxide; n-butyllithium; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen; sodium hydride; In 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)92129-4

upstream raw materials:

((S)-3,4-Dihydroxy-butyl)-phosphonic acid benzyl ester (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

n-hexadecanoyl chloride

1,2:4,5-dicyclohexylidene-myo-inositol

benzyl bromide

Downstream raw materials:

Hexadecanoic acid (R)-1-hexadecanoyloxymethyl-3-[hydroxy-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyloxy)-phosphoryloxy]-propyl ester

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