Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester

Base Information

• Chemical Name: Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester
• CAS No.: 115149-96-7
• Molecular Formula: C₁₉H₁₉O₈P
• Molecular Weight: 406.329
• Mol file: 115149-96-7.mol

Synonyms:Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester

Chemical Property of Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester

There total 3 articles about Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl 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: 28.0%

(4S,6R,7R,8R)-7-hydroxy-6-hydroxymethyl-1,5-dioxa-2-oxobicyclo[3.3.04,8]octane (115149-95-6) + chlorophosphoric acid diphenyl ester (2524-64-3) → Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester (115149-96-7)

Guidance literature:

With dmap; In pyridine; toluene; at -30 - 0 ℃; for 5h;

DOI:10.1016/S0008-6215(00)90891-7

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester (115149-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 24 h / Heating

2: 15 percent / H₂ / 10percent Pd-C / ethanol / 18 h / 2550.2 Torr

3: 28 percent / 4-(dimethylamino)pyridine / toluene; pyridine / 5 h / -30 - 0 °C

With dmap; hydrogen; palladium on activated charcoal; In pyridine; ethanol; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)90891-7

Reference yield:

methyl 3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-D-glycero-D-gulo-heptonate (109065-84-1) → Phosphoric acid (2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydro-furo[3,2-b]furan-2-ylmethyl ester diphenyl ester (115149-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / H₂ / 10percent Pd-C / ethanol / 18 h / 2550.2 Torr

2: 28 percent / 4-(dimethylamino)pyridine / toluene; pyridine / 5 h / -30 - 0 °C

With dmap; hydrogen; palladium on activated charcoal; In pyridine; ethanol; toluene;

DOI:10.1016/S0008-6215(00)90891-7

upstream raw materials:

(4S,6R,7R,8R)-7-hydroxy-6-hydroxymethyl-1,5-dioxa-2-oxobicyclo[3.3.0^4,8]octane

chlorophosphoric acid diphenyl ester

2,3,5-tri-O-benzyl-D-arabinofuranose

methyl 3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-D-glycero-D-gulo-heptonate