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

Base Information

• Chemical Name: diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate
• CAS No.: 176590-52-6
• Molecular Formula: C₃₄H₄₄NO₈P
• Molecular Weight: 625.699
• Mol file: 176590-52-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-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:

acetic anhydride (108-24-7) + ((2S,4R,5S,6R)-3-Amino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid diethyl ester → diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (176590-52-6) + diethyl (((2S,3S,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:

With dmap; In pyridine; for 1h;

DOI:10.1021/jo9519468

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (176590-52-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: zinc dibromide / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: mercury(II) diacetate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: iodine / dichloromethane / 16 h / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: 16 h / 160 °C / Sealed tube

6.1: trifluoroacetic acid; water / dichloromethane / 16 h / 0 - 20 °C

7.1: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C

8.1: acetic acid; hydroxylamine hydrochloride; sodium acetate / water; tetrahydrofuran; methanol / 1 h / pH 4.5

9.1: dmap; pyridine / dichloromethane / 16 h / 20 °C

10.1: borane-THF / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

10.2: 2 h / 0 - 50 °C

10.3: 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; borane-THF; hydroxylamine hydrochloride; mercury(II) diacetate; water; iodine; sodium acetate; acetic anhydride; acetic acid; trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

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,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (176590-52-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid; water / dichloromethane / 16 h / 0 - 20 °C

2.1: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C

3.1: acetic acid; hydroxylamine hydrochloride; sodium acetate / water; tetrahydrofuran; methanol / 1 h / pH 4.5

4.1: dmap; pyridine / dichloromethane / 16 h / 20 °C

5.1: borane-THF / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 - 50 °C

5.3: 16 h / 20 °C

With pyridine; dmap; borane-THF; hydroxylamine hydrochloride; water; sodium acetate; acetic anhydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

upstream raw materials:

acetic anhydride

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

(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol

2,3,5-tri-O-benzyl-D-arabinofuranose

Downstream raw materials:

diethyl C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate

diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate