((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester

Base Information

• Chemical Name: ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester
• CAS No.: 144668-22-4
• Molecular Formula: C₃₀H₃₇O₈P
• Molecular Weight: 556.593
• Mol file: 144668-22-4.mol

Synonyms:((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester

Chemical Property of ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester

There total 3 articles about ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl 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: 91.0%

dimethyl lithiomethylphosphonate (34939-91-8,58648-56-9) + (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one (144668-21-3) → ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester (144668-22-4)

Guidance literature:

In tetrahydrofuran; at -77 ℃; for 0.5h;

DOI:10.1021/jo00051a004

Reference yield:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) → ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester (144668-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / DMSO, acetic anhydride / Ambient temperature

2: 91 percent / tetrahydrofuran / 0.5 h / -77 °C

With acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran;

DOI:10.1021/jo00051a004

Reference yield:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one (144668-21-3) + dimethyl methane phosphonate (756-79-6) → ((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester (144668-22-4)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C to rt;

DOI:10.1080/07328309808001879

upstream raw materials:

dimethyl lithiomethylphosphonate

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one

dimethyl methane phosphonate

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Downstream raw materials:

(1S,4R,5R,6R)-4,5,6-Tris-benzyloxy-3-methyl-cyclohex-2-enol

(1R,4R,5R,6R)-4,5,6-Tris-benzyloxy-3-methyl-cyclohex-2-enol

Phosphoric acid dibenzyl ester (1S,4R,5R,6S)-4,5,6-tris-benzyloxy-3-methyl-cyclohex-2-enyl ester

(4R,5R,6S)-4,5,6-Tris-benzyloxy-3-methyl-cyclohex-2-enone