Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

Base Information

Chemical Name:Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester
CAS No.:183239-89-6
Molecular Formula:C₂₇H₃₄O₈S
Molecular Weight:518.628
Hs Code.:

Synonyms:Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

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Chemical Property of Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

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Technology Process of Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

There total 6 articles about Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-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: 94.0%

: 108-30-5
succinic acid anhydride

: 183239-88-5
Ethyl 3-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-α-L-rhamnopyranoside

: 183239-89-6
Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

Guidance literature:: With pyridine; dmap; for 60h; Ambient temperature;
DOI:10.1002/jlac.199619961016

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 183239-89-6
Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaH, Bu₄NBr / dimethylformamide / 1.) r.t., 45 min, 2.) r.t., 2.5 h

2: 70percent aq. AcOH / 2 h / 60 °C

3: 1.) Bu₂SnO, molecular sieves 4 Angstroem, 2.) CsF / 1.) C₆H₆, reflux, 5 h, 2.) DMF, r.t., 5 h

4: 94 percent / DMAP, pyridine / 60 h / Ambient temperature

With pyridine; dmap; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide; acetic acid; cesium fluoride; In N,N-dimethyl-formamide;
DOI:10.1002/jlac.199619961016

Reference yield:

: 127753-95-1
ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 183239-89-6
Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaH, Bu₄NBr / dimethylformamide / 1.) r.t., 45 min, 2.) r.t., 2.5 h

2: 70percent aq. AcOH / 2 h / 60 °C

3: 1.) Bu₂SnO, molecular sieves 4 Angstroem, 2.) CsF / 1.) C₆H₆, reflux, 5 h, 2.) DMF, r.t., 5 h

4: 94 percent / DMAP, pyridine / 60 h / Ambient temperature

With pyridine; dmap; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide; acetic acid; cesium fluoride; In N,N-dimethyl-formamide;
DOI:10.1002/jlac.199619961016