((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester

Base Information

• Chemical Name: ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester
• CAS No.: 863553-44-0
• Molecular Formula: C₂₄H₂₉O₇P
• Molecular Weight: 460.464
• Mol file: 863553-44-0.mol

Synonyms:((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester

Chemical Property of ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester

There total 4 articles about ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl 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: 60.0%

triethyl phosphite (122-52-1) + 3-benzyloxy-2-benzyloxymethyl-5-iodo-2,3-dihydropyran-4-one (676153-95-0) → ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester (863553-44-0)

Guidance literature:

With nickel dichloride; at 150 ℃; for 5h;

DOI:10.1002/ejoc.200500149

Reference yield:

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester (863553-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / bis(acetoxy)iodobenzene; TsOH / acetonitrile / 1.42 h / 20 °C

2: 60 percent / I₂ / CCl₄; pyridine / 2 h / 20 °C

3: 60 percent / NiCl₂ / 5 h / 150 °C

With [bis(acetoxy)iodo]benzene; iodine; toluene-4-sulfonic acid; nickel dichloride; In pyridine; tetrachloromethane; acetonitrile;

DOI:10.1002/ejoc.200500149

Reference yield:

benzyl bromide (100-39-0) → ((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester (863553-44-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 60 °C

2: 60 percent / bis(acetoxy)iodobenzene; TsOH / acetonitrile / 1.42 h / 20 °C

3: 60 percent / I₂ / CCl₄; pyridine / 2 h / 20 °C

4: 60 percent / NiCl₂ / 5 h / 150 °C

With [bis(acetoxy)iodo]benzene; iodine; sodium hydride; toluene-4-sulfonic acid; nickel dichloride; In tetrahydrofuran; pyridine; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200500149

upstream raw materials:

triethyl phosphite

3-benzyloxy-2-benzyloxymethyl-5-iodo-2,3-dihydropyran-4-one

3,4,6-tri-O-benzyl-D-galactal

benzyl bromide

Downstream raw materials:

C₄₆H₅₃O₁₂P

methyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-diethoxyphosphoryl-α-D-threo-hex-2-enopyranoside

ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-diethoxyphosphoryl-α-D-threo-hex-2-enopyranoside

2'-propyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-diethoxyphosphoryl-α-D-threo-hex-2-enopyranoside