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

Base Information

• Chemical Name: 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
• CAS No.: 502692-49-1
• Molecular Formula: C₅₀H₆₂Cl₃NO₁₇
• Molecular Weight: 1055.4

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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-[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) → 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 (502692-49-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane;

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-[(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 (502692-49-1)

Guidance literature:

Multi-step reaction with 11 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

11.1: 70 percent / 2,3-dichloro-5,6-dicyanoquinone / CH₂Cl₂; aq. phosphate buffer

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; phosphate buffer; 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-[(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 (502692-49-1)

Guidance literature:

Multi-step reaction with 12 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

12.1: 70 percent / 2,3-dichloro-5,6-dicyanoquinone / CH₂Cl₂; aq. phosphate buffer

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; phosphate buffer; 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-[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

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

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

4-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

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