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

Base Information

• Chemical Name: 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
• CAS No.: 419549-86-3
• Molecular Formula: C₈₀H₈₀N₂O₁₇S
• Molecular Weight: 1373.58

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 13 articles about 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 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: 48.0%

perbenzyl fucosyl bromide (33639-77-9) + 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 (419549-85-2) → 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 (419549-86-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -30 ℃; 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-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 (419549-86-3)

Guidance literature:

Multi-step reaction with 12 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

9: Br₂ / CH₂Cl₂ / 0.33 h / 0 °C

10: 330 mg / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 1.5 h / -40 °C

11: 71 percent / [Rh(Ph₃P)3Cl] / ethanol / 5 h / Heating

12: 48 percent / AgOTf; 4 Angstroem molecular sieves; sym-collidine / CH₂Cl₂; toluene / 2 h / -30 °C

With pyridine; 2,4,6-trimethyl-pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; sodium hydride; potassium carbonate; potassium iodide; silver(l) oxide; Wilkinson's catalyst; tris(triphenylphosphine)rhodium(I) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

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

Reference yield:

ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-62-5) → 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 (419549-86-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

2: pyridine / CH₂Cl₂ / 2 h / 0 °C

3: 1.08 g / CH₂Cl₂; dimethylformamide / 5 h / 0 °C

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

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

6: 72 percent / (Ph₃P)3RhCl / ethanol / 3 h / Heating

7: 97 percent / pyridine / 2 h

8: Br₂ / CH₂Cl₂ / 0.33 h / 0 °C

9: 330 mg / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 1.5 h / -40 °C

10: 71 percent / [Rh(Ph₃P)3Cl] / ethanol / 5 h / Heating

11: 48 percent / AgOTf; 4 Angstroem molecular sieves; sym-collidine / CH₂Cl₂; toluene / 2 h / -30 °C

With pyridine; 2,4,6-trimethyl-pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; potassium carbonate; potassium iodide; silver(l) oxide; Wilkinson's catalyst; tris(triphenylphosphine)rhodium(I) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

perbenzyl fucosyl bromide

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 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

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

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