.beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-, 3-(trifluoromethanesulfonate)

Base Information

• Chemical Name: .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-, 3-(trifluoromethanesulfonate)
• CAS No.: 165874-20-4
• Molecular Formula: C25H22 F3 N O9 S
• Molecular Weight: 569.5
• Mol file: 165874-20-4.mol

Synonyms:.beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-, 3-(trifluoromethanesulfonate)

Chemical Property of .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-, 3-(trifluoromethanesulfonate)

Chemical Property:

• PSA: 126.05000
• LogP: 3.94640

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-, 3-(trifluoromethanesulfonate)

There total 1 articles about .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-, 3-(trifluoromethanesulfonate) 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: 84.0%

trifluoromethylsulfonic anhydride (358-23-6) + allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-35-9) → allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-trifluoromethanesulfonyl-β-D-glucopyranoside (165874-20-4)

Guidance literature:

In pyridine; dichloromethane; for 0.5h; -30 deg C to room temperature;

Reference yield: 62.0%

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-trifluoromethanesulfonyl-β-D-glucopyranoside (165874-20-4) → allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranoside (165874-26-0)

Guidance literature:

With tetrabutylammonium nitrite; In N,N-dimethyl-formamide; at 55 ℃; for 3h;

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-trifluoromethanesulfonyl-β-D-glucopyranoside (165874-20-4) → 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (165874-28-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 62 percent / tetrabutylammonium nitrite / dimethylformamide / 3 h / 55 °C

2: 82 percent / NaH / dimethylformamide / 24 h / Ambient temperature

3: 89 percent / 2)2>PF₆ / tetrahydrofuran / 1.5 h

4: 91 percent / HgCl₂ / acetone; H₂O / 3 h / 20 °C

5: 4A MS, DBU / CH₂Cl₂ / 0.25 h / 0 °C

6: 4A MS, trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / -30 °C

7: 1.) DBU, tris(triphenylphosphine)rhodium(I) chloride, 2.) HgCl₂ / 1.) ethanol, benzene, water, reflux, 24 h, 2.) acetone, H₂O, 20 deg C, 3 h

With Wilkinson's catalyst; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetrabutylammonium nitrite; mercury dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

trifluoromethylsulfonic anhydride

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranoside

3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranose

allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranoside

prop-1-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranoside