allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:213912-94-8
Molecular Formula:C₅₉H₅₇NO₁₇
Molecular Weight:1052.1
Hs Code.:

Synonyms:allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 9 articles about allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-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: 89.0%

: 120142-50-9
allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 144367-26-0
6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

: 213912-94-8
allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 0.166667h;
DOI:10.1016/S0008-6215(98)00125-6

Reference yield:

: 120142-50-9
allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: C₃₇H₃₆Cl₃NO₁₁

: 213912-94-8
allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 25 ℃;
DOI:10.1016/0040-4039(95)01162-B

Reference yield:

: 2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6
p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 213912-94-8
allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: NaOMe / methanol / 8 h / pH 10

2: pyridine / 4.5 h / 0 °C

3: pyridine / Ambient temperature

4: p-toluenesulfonic acid / acetonitrile; H₂O / 5 h / pH 3

5: 2-chloro-1-methylpyridinium iodide, 1,4-diazabicyclo<2.2.2>octane / 1,2-dichloro-ethane / 0.33 h

6: 88 percent / ammonium cerium(IV) nitrate / toluene; acetonitrile; H₂O / 0.5 h

7: 89 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

8: 89 percent / 4 Angstroem molecular sieves, Me₃SiOTf / CH₂Cl₂ / 0.17 h

With 1,4-diaza-bicyclo[2.2.2]octane; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;
DOI:10.1016/S0008-6215(98)00125-6