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
Hs Code.:

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

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

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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%

: 129519-28-4
2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

: 106-95-6
allyl bromide

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

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%

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

: 419549-63-6
ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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:

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

: 419549-88-5
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

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