(R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 339317-32-7
• Molecular Formula: C₅₈H₈₃Cl₆N₂O₁₂P
• Molecular Weight: 1243.99
• Mol file: 339317-32-7.mol

Synonyms:

Chemical Property of (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

There total 10 articles about (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-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: 61.0%

trichloroacetonitrile (545-06-2) + (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (474670-20-7) → (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (339317-32-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1016/S0960-894X(02)00362-1

Reference yield:

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (339317-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrazole / CH₂Cl₂

2.1: m-CPBA / CH₂Cl₂ / 0 °C

3.1: [bis(methyldiphenylphosphine)](1,5-cyclooctadiene) iridium(I / tetrahydrofuran

3.2: 79 percent / NBS / tetrahydrofuran; H₂O

4.1: 61 percent / DBU / CH₂Cl₂

With 1H-tetrazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0960-894X(02)00362-1

Reference yield:

lauryl triflate (75618-27-8) → (R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (339317-32-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 68 percent / K₂CO₃ / 1,2-dichloro-ethane

2.1: 86 percent / Zn; AcOH

3.1: 92 percent / EDCI; DMAP / CH₂Cl₂

4.1: 72 percent / BH₃*Me₂NH; BF₃*Et₂O / acetonitrile

5.1: tetrazole / CH₂Cl₂

6.1: m-CPBA / CH₂Cl₂ / 0 °C

7.1: [bis(methyldiphenylphosphine)](1,5-cyclooctadiene) iridium(I / tetrahydrofuran

7.2: 79 percent / NBS / tetrahydrofuran; H₂O

8.1: 61 percent / DBU / CH₂Cl₂

With 1H-tetrazole; dmap; dimethylamine borane; boron trifluoride diethyl etherate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0960-894X(02)00362-1

upstream raw materials:

trichloroacetonitrile

(R)-3-Dodecyloxy-tetradecanoic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Dibenzyl N,N-diisopropylphosphoramidite

lauryl triflate