diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate

Base Information

• Chemical Name: diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate
• CAS No.: 172223-10-8
• Molecular Formula: C₃₂H₃₉O₈P
• Molecular Weight: 582.631
• Mol file: 172223-10-8.mol

Synonyms:diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate

Chemical Property of diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate

There total 7 articles about diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate 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: 83.0%

diethyl (((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)phosphonate (172223-09-5) → diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate (172223-10-8)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide;

DOI:10.1039/c39950001993

Reference yield:

(2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol (160318-52-5) → diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate (172223-10-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.86 g / imidazole / dimethylformamide

2: 77 percent / 5 h / Heating

3: 93 percent / TFA, H₂O / CH₂Cl₂

4: 81 percent / DMSO, Ac₂O

With 1H-imidazole; water; acetic anhydride; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9519468

Reference yield:

diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (172223-08-4) → diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate (172223-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / TFA, H₂O / CH₂Cl₂

2: 81 percent / DMSO, Ac₂O

With water; acetic anhydride; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo9519468

upstream raw materials:

diethyl (((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)phosphonate

(2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol

(((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride

(((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane

Downstream raw materials:

diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

diethyl (((2S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-(hydroxyimino)tetrahydro-2H-pyran-2-yl)methyl)phosphonate