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

Base Information

Chemical Name: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
CAS No.:123574-56-1
Molecular Formula:C₄₀H₅₁Cl₆N₂O₁₅P
Molecular Weight:1043.54
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 93.0%

: 108-24-7
acetic anhydride

: 145609-47-8
2-deoxy-4-O-diphenylphosphono-3-O-(N-dodecanoylglycyl)-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucose

: 123574-56-1
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

Guidance literature:: With pyridine; In dichloromethane; for 19h;
DOI:10.1248/cpb.39.3244

Reference yield:

: 112-16-3
n-dodecanoyl chloride

: 123574-56-1
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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; dmap; sodium hydroxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1248/cpb.39.3244

Reference yield:

: 7596-88-5
N-dodecanoylglycine

: 123574-56-1
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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; dmap; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1248/cpb.39.3244