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

Base Information

Chemical Name: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
CAS No.:147589-19-3
Molecular Formula:C₄₂H₄₉NO₁₁S
Molecular Weight:775.917
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 82.0%

: 147589-18-2
2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

: 77-76-9
2,2-dimethoxy-propane

: 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

Guidance literature:: With toluene-4-sulfonic acid; for 0.5h;
DOI:10.1016/0008-6215(93)87009-H

Reference yield: 81.0%

: 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

: 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

: 147589-21-7
ethyl (3-O-allyl-4,6-O-isopropylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With tetrabutylammonium borohydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1002/1099-0690(200012)2000:23<3931::AID-EJOC3931>3.0.CO;2-W

Reference yield:

: 100-39-0
benzyl bromide

: 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

Guidance literature:: Multi-step reaction with 5 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

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