Dodecanoylamino-acetic 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: Dodecanoylamino-acetic 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.: 133940-55-3
• Molecular Formula: C₃₈H₄₈BrCl₆N₂O₁₃P
• Molecular Weight: 1064.4

Synonyms:

Chemical Property of Dodecanoylamino-acetic 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dodecanoylamino-acetic 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 9 articles about Dodecanoylamino-acetic 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:

1-O-acetyl-2-deoxy-4-O-diphenylphosphono-3-O-(N-dodecanoylglycyl)-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (123574-56-1) → Dodecanoylamino-acetic 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 (133940-55-3)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 3h;

DOI:10.1248/cpb.39.3244

Reference yield:

n-dodecanoyl chloride (112-16-3) → Dodecanoylamino-acetic 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 (133940-55-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / aq. NaOH / 0.5 h

2: 4-dimethylaminopyridine (DMAP), dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 15 h / Ambient temperature

3: 90percent aq. AcOH / 0.33 h / 90 °C

4: 75 percent / pyridine / 1.5 h

5: 87 percent / DMAP, pyridine / 1 h / Ambient temperature

6: 1.) 1,5-cyclooctenebis(methyldiphenylphosphino)iridium hexafluorophosphate, H₂, 2.) aq. I₂ / 1.) THF, 50 deg C, 2 h, 2.) THF, 30 min

7: 93 percent / pyridine / CH₂Cl₂ / 19 h

8: 25percent HBr/AcOH / CH₂Cl₂ / 3 h

With pyridine; dmap; sodium hydroxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen bromide; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1248/cpb.39.3244

Reference yield:

N-dodecanoylglycine (7596-88-5) → Dodecanoylamino-acetic 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 (133940-55-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-dimethylaminopyridine (DMAP), dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 15 h / Ambient temperature

2: 90percent aq. AcOH / 0.33 h / 90 °C

3: 75 percent / pyridine / 1.5 h

4: 87 percent / DMAP, pyridine / 1 h / Ambient temperature

5: 1.) 1,5-cyclooctenebis(methyldiphenylphosphino)iridium hexafluorophosphate, H₂, 2.) aq. I₂ / 1.) THF, 50 deg C, 2 h, 2.) THF, 30 min

6: 93 percent / pyridine / CH₂Cl₂ / 19 h

7: 25percent HBr/AcOH / CH₂Cl₂ / 3 h

With pyridine; dmap; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen bromide; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1248/cpb.39.3244

upstream raw materials:

1-O-acetyl-2-deoxy-4-O-diphenylphosphono-3-O-(N-dodecanoylglycyl)-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

n-dodecanoyl chloride

N-dodecanoylglycine

allyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Downstream raw materials:

C₈₆H₁₂₄Cl₆N₄O₂₅P₂

C₉₁H₁₂₉Cl₆N₄O₂₅P

C₈₆H₁₂₃Cl₆N₅O₂₆P₂

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