((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester

Base Information

• Chemical Name: ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester
• CAS No.: 211134-54-2
• Molecular Formula: C₃₁H₄₅O₁₄P
• Molecular Weight: 672.664
• Mol file: 211134-54-2.mol

Synonyms:

Chemical Property of ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester

There total 8 articles about ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-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:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester (211134-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: PCl₃ / pyridine; hexane / 2 h / 20 °C

1.2: 70 percent / H₂O; pyridine / hexane / 10 h / 20 °C

2.1: DBU / 0 - 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; phosphorus trichloride; In pyridine; hexane; 1.1: Substitution / 1.2: Hydrolysis / 2.1: Addition;

DOI:10.1007/BF02496414

Reference yield:

benzaldehyde (100-52-7) + tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite (10424-85-8) → ((S)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester + ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester (211134-54-2)

Guidance literature:

With chloro-trimethyl-silane; at 0 - 20 ℃;

DOI:10.1007/BF02496414

Reference yield:

benzaldehyde (100-52-7) + (-)-bis(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite (181530-80-3) → ((S)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester + ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester (211134-54-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 0 - 20 ℃;

DOI:10.1007/BF02496414

upstream raw materials:

benzaldehyde

(-)-bis(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite

tris(1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) phosphite

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

(+)-(R)-1-phenyl-1-hydroxymethylphosphonic acid