ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS No.: 419549-69-2
• Molecular Formula: C₃₂H₃₃NO₇S
• Molecular Weight: 575.683
• Mol file: 419549-69-2.mol

Synonyms:ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Chemical Property of ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

There total 8 articles about ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 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: 97.0%

acetic anhydride (108-24-7) + ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-68-1) → ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-69-2)

Guidance literature:

With pyridine; for 2h;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4) → ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-69-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / NaH / tetrahydrofuran

2: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 1.08 g / CH₂Cl₂; dimethylformamide / 5 h / 0 °C

5: 73 percent / K₂CO₃ / methanol; tetrahydrofuran / 4 h

6: 82 percent / Ag₂O; KI; 4 Angstroem molecular sieves / dimethylformamide / 5 h / 0 °C

7: 72 percent / (Ph₃P)3RhCl / ethanol / 3 h / Heating

8: 97 percent / pyridine / 2 h

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium hydride; potassium carbonate; potassium iodide; silver(l) oxide; Wilkinson's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-63-6) → ethyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-69-2)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 1.08 g / CH₂Cl₂; dimethylformamide / 5 h / 0 °C

3: 73 percent / K₂CO₃ / methanol; tetrahydrofuran / 4 h

4: 82 percent / Ag₂O; KI; 4 Angstroem molecular sieves / dimethylformamide / 5 h / 0 °C

5: 72 percent / (Ph₃P)3RhCl / ethanol / 3 h / Heating

6: 97 percent / pyridine / 2 h

With pyridine; 4 A molecular sieve; potassium carbonate; potassium iodide; silver(l) oxide; Wilkinson's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

upstream raw materials:

acetic anhydride

ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl (4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside