Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester
CAS No.:870001-81-3
Molecular Formula:C₃₁H₃₁NO₈S
Molecular Weight:577.655
Hs Code.:

Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

Synonyms:Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester 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%

: p-tolyl 3-O-acetyl-1,2-deoxy-4,6-O-(p-methoxybenzylidene)-2-phthalimido-1-thio-β-D-glucopyranoside

: 870001-81-3
Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With borane-THF; di-n-butylboryl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at -20 - -5 ℃; for 1.5h;
DOI:10.1021/ol052130o

Reference yield: 88.0%

: 870001-81-3
Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

: 58479-61-1
tert-butylchlorodiphenylsilane

: 870001-82-4
Acetic acid (2R,3S,4R,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxy-benzyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/ol052130o

Reference yield:

: 870001-81-3
Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

: (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-6-sulfooxymethyl-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: NaOMe / CH₂Cl₂; methanol / 4 h / 20 °C

3.1: ethylenediamine / butan-1-ol / 12 h / 100 °C

4.1: 0.600 g / CuSO₄*5H₂O; potassium carbonate; TfN₃ / methanol; H₂O / 48 h / 20 °C

5.1: 90 percent / DCC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: N-benzenesulfinyl piperidine; Tf₂O; molecular sieves 4 Angstroem / DTBMP / CH₂Cl₂ / -60 °C

6.2: 25 percent / CH₂Cl₂ / 20 h / -60 - 20 °C

7.1: 80 percent / TBAF; HF*pyridine / tetrahydrofuran / 0 - 20 °C

8.1: pyridine; SO₃*NMe₃ / 20 h / 55 °C

With pyridine; 1H-imidazole; dmap; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; trimethyl-sulfo-ammonium betaine; 4 A molecular sieve; triflic azide; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; pyridine hydrogenfluoride; copper(II) sulfate; ethylenediamine; dicyclohexyl-carbodiimide; 2,6-di-tert-butyl-4-methylpyridine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1021/ol052130o