(R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate

Base Information

• Chemical Name: (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate
• CAS No.: 185855-11-2
• Molecular Formula: C₂₅H₃₅O₇P
• Molecular Weight: 478.522
• Mol file: 185855-11-2.mol

Synonyms:(R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate

Chemical Property of (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate

There total 4 articles about (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate 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-cyclohexylidene-α-D-glucofuranose (23397-76-4) + methyl(phenyl)phosphinic chloride (5761-97-7) → (S)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate (185855-09-8) + (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate (185855-11-2)

Guidance literature:

With triethylamine; In toluene; at -78 ℃; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(99)00171-9

Reference yield:

methyl methylphenylphosphinate (6389-79-3) → (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate (185855-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / phosphorus pentachloride / CCl₄ / 3 h / Heating

2: pyridine / tetrahydrofuran / 0 - 20 °C

With pyridine; phosphorus pentachloride; In tetrahydrofuran; tetrachloromethane;

DOI:10.1021/jo052575q

Reference yield:

dimethyl phenylphosphonate (2240-41-7) → (R)-1,2:5,6-di-O-cyclohexylidene-D-glucose methyl phenyl phosphinate (185855-11-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 18 h / Reflux; Inert atmosphere

2.1: phosphorus pentachloride / tetrachloromethane / Inert atmosphere

3.1: pyridine / toluene / 0.67 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

With pyridine; phosphorus pentachloride; In tetrachloromethane; toluene;

DOI:10.1002/ejoc.201501260

upstream raw materials:

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

methyl(phenyl)phosphinic chloride

methyl methylphenylphosphinate

dimethyl phenylphosphonate

Downstream raw materials:

(-)-(S_P)-methylphenylvinylphosphine oxide