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

Base Information

• Chemical Name: 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
• CAS No.: 183240-07-5
• Molecular Formula: C₅₂H₅₈ClNO₁₆
• Molecular Weight: 988.483

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 13 articles about 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 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: 55.0%

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 (183239-98-7) → Benzoic acid (1R,3S,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[13.4.0.03,8]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[13.4.0.03,8]nonadec-16-yl ester (183240-07-5)

Guidance literature:

With N-iodo-succinimide; 3 A molecular sieve; In acetonitrile; at 0 ℃; for 21h;

DOI:10.1002/jlac.199619961016

Reference yield:

benzyl bromide (100-39-0) → 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[13.4.0.03,8]nonadec-16-yl ester (183240-07-5)

Guidance literature:

Multi-step reaction with 7 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

6: 75 percent / HCl, NaCNBH₃ / tetrahydrofuran; diethyl ether / 0.08 h / Ambient temperature

7: 55 percent / N-iodosuccinimide, molecular sieves 3 Angstroem / acetonitrile / 21 h / 0 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; 3 A molecular sieve; 4 A molecular sieve; di(n-butyl)tin oxide; sodium cyanoborohydride; dicyclohexyl-carbodiimide; cesium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1002/jlac.199619961016

Reference yield:

benzoyl chloride (98-88-4) → 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[13.4.0.03,8]nonadec-16-yl ester (183240-07-5)

Guidance literature:

Multi-step reaction with 6 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

5: 75 percent / HCl, NaCNBH₃ / tetrahydrofuran; diethyl ether / 0.08 h / Ambient temperature

6: 55 percent / N-iodosuccinimide, molecular sieves 3 Angstroem / acetonitrile / 21 h / 0 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; N-iodo-succinimide; 3 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1002/jlac.199619961016

upstream raw materials:

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

benzyl bromide

benzoyl chloride

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

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

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