allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside
• CAS No.: 135271-13-5
• Molecular Formula: C₇₉H₁₁₄F₂NO₁₇P
• Molecular Weight: 1418.74
• Mol file: 135271-13-5.mol

Synonyms:

Chemical Property of allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside

There total 1 articles about allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside 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: 95.0%

allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside (132792-05-3,135271-12-4,135271-14-6) + chlorophosphoric acid diphenyl ester (2524-64-3) → allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside (132792-06-4,135271-13-5,135271-15-7)

Guidance literature:

With dmap; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/jm00112a045

Reference yield:

allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside (132792-06-4,135271-13-5,135271-15-7) → 2-deoxy-2-<(R)-(2,2-difluoro-3-hydroxytetradecanoyl)amino>-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-D-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 8H₁₂(Ir(PMePh₂)2>PF₆, 2.) concd. HCl / 1.) THF, 20 deg C, 2 h, 2.) THF, 50 deg C, 3 h

2: 31 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

With hydrogenchloride; PF6; hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jm00112a045

Reference yield:

allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside (132792-06-4,135271-13-5,135271-15-7) → 2-deoxy-2-<(S)-(2,2-difluoro-3-hydroxytetradecanoyl)amino>-4-O-(diphenylphosphoryl)-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-D-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 8H₁₂(Ir(PMePh₂)2>PF₆, 2.) concd. HCl / 1.) THF, 20 deg C, 2 h, 2.) THF, 50 deg C, 3 h

2: 35 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

With hydrogenchloride; PF6; hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jm00112a045

upstream raw materials:

allyl 6-O-(benzyloxycarbonyl)-2-<(RS)-<3-<(benzyloxycarbonyl)oxy>-2,2-difluorotetradecanoyl>amino>-2-deoxy-3-O-<(R)-3-(tetradecanoyloxy)tetradecanoyl>-β-D-glucopyranoside

chlorophosphoric acid diphenyl ester