Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

Base Information

Chemical Name:Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester
CAS No.:82755-04-2
Molecular Formula:C₅₀H₈₃NO₈
Molecular Weight:826.211
Hs Code.:

Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

Synonyms:Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

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Chemical Property of Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

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Technology Process of Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

There total 10 articles about Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl 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: 85.0%

: 82755-03-1
1-propenyl 3-O-benzyl-4-O-levulinoyl-6-O-palmitoyl-2-deoxy-2-(palmitoylamino)-β-D-glucopyranoside

: 82755-04-2
Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

Guidance literature:: With mercury dichloride; mercury(II) oxide; In acetonitrile; at 80 ℃; for 0.666667h;
DOI:10.1016/S0040-4039(00)87231-7

Reference yield:

: 40608-06-8
levulinic anhydride

: 82755-04-2
Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / 4-(dimethylamino)pyridine / pyridine; dioxane / 0.5 h / 20 °C

2: 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate / tetrahydrofuran / 4 h / 30 - 35 °C

3: 85 percent / HgCl₂, HgO / acetonitrile / 0.67 h / 80 °C

With dmap; mercury dichloride; mercury(II) oxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; acetonitrile;

Reference yield:

: 82754-99-2
allyl 3-O-benzyl-4,6-O-isopropylidene-2-deoxy-2-(palmitoylamino)-β-D-glucopyranoside

: 82755-04-2
Hexadecanoic acid (3aR,5R,6S,7R,7aR)-7-benzyloxy-6-(4-oxo-pentanoyloxy)-2-pentadecyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: acetic acid; H₂O / 0.33 h / 90 °C

2: pyridine / CH₂Cl₂ / 1.) 2 h, -15 deg C; 2.) 20 deg C, 15 min

3: 88 percent / 4-(dimethylamino)pyridine / pyridine; dioxane / 0.5 h / 20 °C

4: 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate / tetrahydrofuran / 4 h / 30 - 35 °C

5: 85 percent / HgCl₂, HgO / acetonitrile / 0.67 h / 80 °C

With pyridine; dmap; mercury dichloride; mercury(II) oxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water; acetic acid; acetonitrile;