(R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 339317-28-1
• Molecular Formula: C₄₅H₇₂Cl₃NO₉
• Molecular Weight: 877.427
• Mol file: 339317-28-1.mol

Synonyms:(R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 4 articles about (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 92.0%

(R)-3-(dodecanoyloxy)tetradecanoic acid (338952-12-8) + allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (183388-21-8) → (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (339317-28-1)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

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

Reference yield:

lauryl triflate (75618-27-8) → (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (339317-28-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 86 percent / Zn; AcOH

3: 92 percent / EDCI; DMAP / CH₂Cl₂

With dmap; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In dichloromethane; 1,2-dichloro-ethane;

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

Reference yield:

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → (R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (339317-28-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 86 percent / Zn; AcOH

3: 92 percent / EDCI; DMAP / CH₂Cl₂

With dmap; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In dichloromethane; 1,2-dichloro-ethane;

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

upstream raw materials:

(R)-3-(dodecanoyloxy)tetradecanoic acid

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

lauryl triflate

(3R)-3-hydroxytetradecanoic acid phenacyl ester

Downstream raw materials:

(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

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

(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

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