2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride

Base Information

• Chemical Name: 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride
• CAS No.: 503831-01-4
• Molecular Formula: C₄₉H₄₉Cl₃FNO₁₀
• Molecular Weight: 937.286
• Mol file: 503831-01-4.mol

Synonyms:2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride

Chemical Property of 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride

There total 16 articles about 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride 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: 93.0%

2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-D-glucopyranoside → 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride (503831-01-4)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/j.tet.2003.08.047

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride (503831-01-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 0.87 g / p-TsOH / acetonitrile / 1 h / 20 °C

2: 91 percent / NaH / tetrahydrofuran / 60 °C

3: 95 percent / Zn; AcOH / CH₂Cl₂ / 3 h / 20 °C

4: 87 percent / pyridine / 0 °C

5: 90 percent / n-Bu₄NF / tetrahydrofuran; acetic acid / 20 °C

6: 93 percent / Et₂NSF₃ / tetrahydrofuran / 0.5 h / 0 °C

With diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; acetic acid; zinc; In tetrahydrofuran; pyridine; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/j.tet.2003.08.047

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride (503831-01-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / AgOTf / 1,2-dichloro-ethane / 3.5 h / -15 °C

2: NaOMe / methanol / 1 h / 20 °C

3: 0.87 g / p-TsOH / acetonitrile / 1 h / 20 °C

4: 91 percent / NaH / tetrahydrofuran / 60 °C

5: 95 percent / Zn; AcOH / CH₂Cl₂ / 3 h / 20 °C

6: 87 percent / pyridine / 0 °C

7: 90 percent / n-Bu₄NF / tetrahydrofuran; acetic acid / 20 °C

8: 93 percent / Et₂NSF₃ / tetrahydrofuran / 0.5 h / 0 °C

With diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/j.tet.2003.08.047

upstream raw materials:

N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-hydroxy-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide

benzaldehyde dimethyl acetal

tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside

tert-butyldiphenylsilyl 4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside