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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name: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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:183239-94-3
Molecular Formula:C₅₂H₆₁NO₁₅S
Molecular Weight:972.12
Hs Code.:

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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Synonyms: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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of 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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of 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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 10 articles about 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-hydroxy-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: 98.0%

: 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

: 183239-94-3
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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 16h; Ambient temperature;
DOI:10.1002/jlac.199619961016

Reference yield:

: 100-39-0
benzyl bromide

: 183239-94-3
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-hydroxy-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: 98 percent / aq. DDQ / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; dmap; 4 A molecular sieve; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1002/jlac.199619961016

Reference yield:

: 98-88-4
benzoyl chloride

: 183239-94-3
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-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 53 percent / Bu₄NHSO₄, 5percent aq. NaOH / CH₂Cl₂ / 0.33 h / -4 °C

2: 88 percent / DCC, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

3: 98 percent / aq. DDQ / CH₂Cl₂ / 16 h / Ambient temperature

With dmap; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1002/jlac.199619961016