ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:147589-20-6
Molecular Formula:C₄₂H₄₇NO₁₁S
Molecular Weight:773.901
Hs Code.:

Synonyms:ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 7 articles about ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-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: 87.0%

: 147589-19-3
ethyl (3-O-allyl-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 147589-20-6
ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With acetic anhydride; dimethyl sulfoxide; for 16h; Ambient temperature;
DOI:10.1016/0008-6215(93)87009-H

Reference yield:

: 100-39-0
benzyl bromide

: 147589-20-6
ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / NaH / tetrahydrofuran / 1 h / Heating

2: 1.) borane-trimethylamine complex, 4 Angstroem molecular sieves, 2.) AlCl₃ / 1.) THF, 1 h, 2.) 5 h

3: 1.) 4 Angstroem molecular sieves, 2.) silver triflate / 1.) CH₂Cl₂, toluene, 30 min, 2.) toluene, -40 deg C, 2 h

4: 99 percent / NaOMe / methanol

5: 82 percent / p-toluenesulfonic acid monohydrate / 0.5 h

6: 87 percent / Ac₂O-Me₂SO / 16 h / Ambient temperature

With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol;
DOI:10.1016/0008-6215(93)87009-H

Reference yield:

: 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

: 147589-20-6
ethyl 4-O-(3-O-allyl-4,6-O-isopropylidene-β-D-arabino-hexopyranosyl-2-ulose)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / NaH / tetrahydrofuran / 1 h / Heating

2: 1.) borane-trimethylamine complex, 4 Angstroem molecular sieves, 2.) AlCl₃ / 1.) THF, 1 h, 2.) 5 h

3: 1.) 4 Angstroem molecular sieves, 2.) silver triflate / 1.) CH₂Cl₂, toluene, 30 min, 2.) toluene, -40 deg C, 2 h

4: 99 percent / NaOMe / methanol

5: 82 percent / p-toluenesulfonic acid monohydrate / 0.5 h

6: 87 percent / Ac₂O-Me₂SO / 16 h / Ambient temperature

With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol;
DOI:10.1016/0008-6215(93)87009-H