Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (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 (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:183239-96-5
Molecular Formula:C₆₀H₇₁NO₁₆S
Molecular Weight:1094.29
Hs Code.:

Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (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 (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (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 (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 11 articles about Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (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: 35.0%

: 183239-93-2
Succinic acid (2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

: 183239-97-6
Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

: 183239-96-5
Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 0.0833333h; Ambient temperature;
DOI:10.1002/jlac.199619961016

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 183239-96-5
Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (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 6 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

5: 88 percent / DCC, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

6: 35 percent / HCl, NaCNBH₃, molecular sieves 3 Angstroem / diethyl ether; tetrahydrofuran / 0.08 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; acetic acid; dicyclohexyl-carbodiimide; cesium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/jlac.199619961016

Reference yield:

: 100-39-0
benzyl bromide

: 183239-96-5
Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (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: 1.) Bu₂SnO, molecular sieves 4 Angstroem, 2.) CsF / 1.) C₆H₆, reflux, 5 h, 2.) DMF, r.t., 5 h

2: 94 percent / DMAP, pyridine / 60 h / Ambient temperature

3: 88 percent / DCC, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

4: 35 percent / HCl, NaCNBH₃, molecular sieves 3 Angstroem / diethyl ether; tetrahydrofuran / 0.08 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; 3 A molecular sieve; 4 A molecular sieve; di(n-butyl)tin oxide; sodium cyanoborohydride; dicyclohexyl-carbodiimide; cesium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1002/jlac.199619961016