(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester
CAS No.:137600-40-9
Molecular Formula:C₄₁H₅₀BrCl₉NO₁₅P
Molecular Weight:1226.8
Hs Code.:

(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

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Chemical Property of (R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

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Technology Process of (R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

There total 11 articles about (R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl 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:

: 28715-21-1,3422-31-9
(R)-3-hydroxytetradecanoic acid

: 137600-40-9
(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 61 percent / triethylamine / ethyl acetate / 72 h / Ambient temperature

2: pyridine / Ambient temperature; 1) THF, 1 h 2) methanol, 1 h

3: H₂ / Pd/C / tetrahydrofuran / 2 h

4: 75 percent / dimethylaminopyridine (DMAP), dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 1 h / Ambient temperature

5: 91 percent / 90percent AcOH / 0.5 h / 90 °C

6: 85 percent / pyridine / 6 h / Ambient temperature

7: 95 percent / dimethylaminopyridine (DMAP), pyridine / CH₂Cl₂ / 22 h / Ambient temperature

8: 1) 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate / H₂ 2) I₂ / H₂O / 1) THF, 50 deg C, 2 h, 2) 20 min, r.t.

9: 100 percent / pyridine / CH₂Cl₂ / 15 h / Ambient temperature

10: HBr/25percent AcOH / CH₂Cl₂ / 1.5 h / Ambient temperature

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen bromide; hydrogen; iodine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1248/cpb.39.1994

Reference yield:

: 88862-84-4
3-hydroxy-D-tetradecanoic acid benzyl ester

: 137600-40-9
(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / Ambient temperature; 1) THF, 1 h 2) methanol, 1 h

2: H₂ / Pd/C / tetrahydrofuran / 2 h

3: 75 percent / dimethylaminopyridine (DMAP), dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 1 h / Ambient temperature

4: 91 percent / 90percent AcOH / 0.5 h / 90 °C

5: 85 percent / pyridine / 6 h / Ambient temperature

6: 95 percent / dimethylaminopyridine (DMAP), pyridine / CH₂Cl₂ / 22 h / Ambient temperature

7: 1) 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate / H₂ 2) I₂ / H₂O / 1) THF, 50 deg C, 2 h, 2) 20 min, r.t.

8: 100 percent / pyridine / CH₂Cl₂ / 15 h / Ambient temperature

9: HBr/25percent AcOH / CH₂Cl₂ / 1.5 h / Ambient temperature

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen bromide; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.39.1994

Reference yield:

: (R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid benzyl ester

: 137600-40-9
(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / Pd/C / tetrahydrofuran / 2 h

2: 75 percent / dimethylaminopyridine (DMAP), dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 1 h / Ambient temperature

3: 91 percent / 90percent AcOH / 0.5 h / 90 °C

4: 85 percent / pyridine / 6 h / Ambient temperature

5: 95 percent / dimethylaminopyridine (DMAP), pyridine / CH₂Cl₂ / 22 h / Ambient temperature

6: 1) 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate / H₂ 2) I₂ / H₂O / 1) THF, 50 deg C, 2 h, 2) 20 min, r.t.

7: 100 percent / pyridine / CH₂Cl₂ / 15 h / Ambient temperature

8: HBr/25percent AcOH / CH₂Cl₂ / 1.5 h / Ambient temperature

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen bromide; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.39.1994