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

Base Information

• Chemical Name: ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 419549-62-5
• Molecular Formula: C₂₆H₂₇NO₆S
• Molecular Weight: 481.569
• Mol file: 419549-62-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about ethyl 3-O-allyl-4,6-O-benzylidene-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: 80.0%

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) + allyl bromide (106-95-6) → ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-62-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

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

Reference yield: 85.0%

ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-62-5) → ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-63-6)

Guidance literature:

With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; In tetrahydrofuran; at 20 ℃; for 6h;

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 (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 (419549-88-5)

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: 67 percent / AcCl; MeOH / CH₂Cl₂ / 72 h / 20 °C

With pyridine; methanol; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; potassium carbonate; acetyl chloride; 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:

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

allyl bromide

Downstream raw materials:

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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