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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 183239-95-4
• Molecular Formula: C₅₄H₆₂ClNO₁₆S
• Molecular Weight: 1048.6
• Mol file: 183239-95-4.mol

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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester

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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester

There total 11 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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-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%

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 (183239-94-3) + Chloroacetic anhydride (541-88-8) → 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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester (183239-95-4)

Guidance literature:

With pyridine; at 0 ℃; for 1h;

DOI:10.1002/jlac.199619961016

Reference yield:

benzyl bromide (100-39-0) → 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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester (183239-95-4)

Guidance literature:

Multi-step reaction with 5 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

5: 94 percent / pyridine / 1 h / 0 °C

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:

benzoyl chloride (98-88-4) → 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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester (183239-95-4)

Guidance literature:

Multi-step reaction with 4 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

4: 94 percent / pyridine / 1 h / 0 °C

With pyridine; 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

upstream raw materials:

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

Chloroacetic anhydride

benzyl bromide

benzoyl chloride

Downstream raw materials:

Benzoic acid (1R,3R,5S,6S,7R,8R,15S,16R,17R,19R)-7-benzyloxy-17-(5-benzyloxycarbonylamino-pentyloxy)-19-benzyloxymethyl-6-hydroxy-5-methyl-10,13-dioxo-2,4,9,14,18-pentaoxa-tricyclo[13.4.0.0^3,8]nonadec-16-yl ester

Benzoic acid (1R,3R,5S,6S,7R,8R,15S,16R,17R,19R)-7-benzyloxy-17-(5-benzyloxycarbonylamino-pentyloxy)-19-benzyloxymethyl-6-(2-chloro-acetoxy)-5-methyl-10,13-dioxo-2,4,9,14,18-pentaoxa-tricyclo[13.4.0.0^3,8]nonadec-16-yl ester

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-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester