6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Base Information

• Chemical Name: 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester
• CAS No.: 502692-48-0
• Molecular Formula: C₅₈H₇₀Cl₃NO₁₈
• Molecular Weight: 1175.55

Synonyms:6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Chemical Property of 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

There total 11 articles about 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl 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: 70.0%

6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (502692-40-2) + 4-Oxo-pentanoic acid (2S,3R,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-3-yl ester (502692-36-6) → 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (502692-48-0)

Guidance literature:

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; at -45 ℃;

DOI:10.1002/1521-3773(20021104)41:21<4098::AID-ANIE4098>3.0.CO;2-P

Reference yield:

p-methylphenyl-1-thio-β-D-galactopyranoside (1152-39-2,28244-98-6,121523-95-3,131488-68-1) → 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (502692-48-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: imidazole; N,N-dimethylformamide

2.1: camphorsulfonic acid / acetone

3.1: pyridine / CH₂Cl₂

4.1: CH₃COOH / H₂O / 80 °C

5.1: (n-C₄H₉)2SnO / benzene; toluene / 18 h / 120 °C

5.2: (n-C₄H₉)4NI / toluene / 6 h / 90 °C

6.1: tetrabutylammonium fluoride / tetrahydrofuran

7.1: 90 percent / NaH; (n-C₄H₉)4NI; N,N-dimethylformamide

8.1: NaOCH₃; CH₃OH / CH₂Cl₂

9.1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 4-dimethylaminopyridine

10.1: 70 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves / -45 °C

With pyridine; 1H-imidazole; methanol; dmap; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; benzene; 8.1: Zemplen deacylation;

DOI:10.1002/1521-3773(20021104)41:21<4098::AID-ANIE4098>3.0.CO;2-P

Reference yield:

4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → 6-[4-acetoxy-5-[5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (502692-48-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaOCH₃; CH₃OH / CH₂Cl₂

2.1: imidazole; N,N-dimethylformamide

3.1: camphorsulfonic acid / acetone

4.1: pyridine / CH₂Cl₂

5.1: CH₃COOH / H₂O / 80 °C

6.1: (n-C₄H₉)2SnO / benzene; toluene / 18 h / 120 °C

6.2: (n-C₄H₉)4NI / toluene / 6 h / 90 °C

7.1: tetrabutylammonium fluoride / tetrahydrofuran

8.1: 90 percent / NaH; (n-C₄H₉)4NI; N,N-dimethylformamide

9.1: NaOCH₃; CH₃OH / CH₂Cl₂

10.1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 4-dimethylaminopyridine

11.1: 70 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves / -45 °C

With pyridine; 1H-imidazole; methanol; dmap; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; benzene; 1.1: Zemplen deacylation / 9.1: Zemplen deacylation;

DOI:10.1002/1521-3773(20021104)41:21<4098::AID-ANIE4098>3.0.CO;2-P

upstream raw materials:

6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

4-Oxo-pentanoic acid (2S,3R,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-3-yl ester

p-methylphenyl-1-thio-β-D-galactopyranoside

4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

6-[(2R,3R,4R,5S,6R)-4-Acetoxy-5-[(2S,3R,4S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

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