1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate)

Base Information

• Chemical Name: 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate)
• CAS No.: 97562-27-1
• Molecular Formula: C₅₄H₇₈Cl₆NO₁₆P
• Molecular Weight: 1240.9

Synonyms:

Chemical Property of 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate)

There total 20 articles about 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate) 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:

(R)-3-(dodecanoyloxy)tetradecanoic acid (87357-76-4) → 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate) (97562-27-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 4-dimethylaminopyridine, dicyclohexylcarbodiimide, 2.) 90percent acetic acid / 1.) dichloromethane, room temp., 2 h, 2.) 95 deg C, 10 min

2: 61 percent / pyridine / 0.33 h

3: 89 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) 1,5-cyclooctadienebis(methyldiphenylphosphine)-iridium hexafluorophosphate, H₂, 2.) H₂O, I₂ / 1.) THF, 50 deg C, 40 min, 2.) THF, room temp., 10 min, 3.) anhydrous CHCl₃

5: pyridine / CHCl₃

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; In pyridine; dichloromethane; chloroform;

DOI:10.1246/bcsj.60.2205

Reference yield:

allyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (97562-24-8) → 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate) (97562-27-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 4-dimethylaminopyridine, dicyclohexylcarbodiimide, 2.) 90percent acetic acid / 1.) dichloromethane, room temp., 2 h, 2.) 95 deg C, 10 min

2: 61 percent / pyridine / 0.33 h

3: 89 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) 1,5-cyclooctadienebis(methyldiphenylphosphine)-iridium hexafluorophosphate, H₂, 2.) H₂O, I₂ / 1.) THF, 50 deg C, 40 min, 2.) THF, room temp., 10 min, 3.) anhydrous CHCl₃

5: pyridine / CHCl₃

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; In pyridine; dichloromethane; chloroform;

DOI:10.1246/bcsj.60.2205

Reference yield:

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → 1-O-acetyl-2-deoxy-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 4-(diphenyl phosphate) (97562-27-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) pyridine, 2.) zinc powder, acetic acid / 1.) 1 h, room temp., 2.) 50 deg C, 3 h

2: 1.) 4-dimethylaminopyridine, dicyclohexylcarbodiimide, 2.) 90percent acetic acid / 1.) dichloromethane, room temp., 2 h, 2.) 95 deg C, 10 min

3: 61 percent / pyridine / 0.33 h

4: 89 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) 1,5-cyclooctadienebis(methyldiphenylphosphine)-iridium hexafluorophosphate, H₂, 2.) H₂O, I₂ / 1.) THF, 50 deg C, 40 min, 2.) THF, room temp., 10 min, 3.) anhydrous CHCl₃

6: pyridine / CHCl₃

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen; iodine; acetic acid; dicyclohexyl-carbodiimide; zinc; In pyridine; dichloromethane; chloroform;

DOI:10.1246/bcsj.60.2205

upstream raw materials:

acetic anhydride

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

(+)-D-glucosamine hydrochloride

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

Downstream raw materials:

(R)-3-Tetradecanoyloxy-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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