diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

Base Information

Chemical Name:diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate
CAS No.:1365769-28-3
Molecular Formula:C₃₈H₄₂O₁₆
Molecular Weight:754.742
Hs Code.:

Synonyms:diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

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Chemical Property of diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

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Technology Process of diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

There total 5 articles about diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate 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: 91.0%

: 1365769-39-6
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 105-53-3
diethyl malonate

: 1365769-28-3
diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

Guidance literature:: With piperidine; In acetonitrile; at 65 ℃; for 28h; Molecular sieve;
DOI:10.1021/ja3004045

Reference yield:

: 74808-10-9,86520-63-0,92052-29-4,121238-27-5,127061-80-7,142831-80-9,87119-53-7
O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate

: 1365769-28-3
diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -42 °C / Inert atmosphere; Molecular sieve

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 85 °C / Inert atmosphere

2.2: 30 h / 65 °C

3.1: piperidine / acetonitrile / 28 h / 65 °C / Molecular sieve

With piperidine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; In tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1002/anie.201408560

Reference yield:

: 106-44-5
p-cresol

: 1365769-28-3
diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -42 °C / Inert atmosphere; Molecular sieve

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 85 °C / Inert atmosphere

2.2: 30 h / 65 °C

3.1: piperidine / acetonitrile / 28 h / 65 °C / Molecular sieve

With piperidine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; In tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1002/anie.201408560