dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate

Base Information

• Chemical Name: dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate
• CAS No.: 115221-69-7
• Molecular Formula: C₃₁H₃₈NO₈P
• Molecular Weight: 583.618
• Mol file: 115221-69-7.mol

Synonyms:dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate

Chemical Property of dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate

There total 3 articles about dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)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: 92.0%

acetic anhydride (108-24-7) + ((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-nitro-tetrahydro-pyran-2-yl)-phosphonic acid dimethyl ester → dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate (115221-69-7)

Guidance literature:

((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-nitro-tetrahydro-pyran-2-yl)-phosphonic acid dimethyl ester; With hydrogen; nickel; platinum; In ethanol;

acetic anhydride; at 20 ℃; Further stages.;

DOI:10.1002/ejoc.200400266

Reference yield:

3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate (115221-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuOK / toluene / 0.08 h / 0 °C

2.1: H₂ / Pt/Raney-Ni / ethanol

2.2: 92 percent / 20 °C

With potassium tert-butylate; hydrogen; nickel; platinum; In ethanol; toluene; 1.1: Michael-type addition;

DOI:10.1002/ejoc.200400266

Reference yield:

dimethyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl) phosphonate (115221-65-3) → dimethyl (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)phosphonate (115221-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄, NiCl₂*6H₂O, H₃BO₃ / ethanol / 14 h / Ambient temperature

2: 19 h / Ambient temperature

With sodium tetrahydroborate; boric acid; nickel dichloride; In ethanol;

DOI:10.1002/hlca.19870700516

upstream raw materials:

acetic anhydride

3,4,6-tri-O-benzyl-2-nitro-D-galactal

dimethyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl) phosphonate