9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS No.: 203794-79-0
• Molecular Formula: C₅₉H₇₃NO₁₄
• Molecular Weight: 1020.23

Synonyms:9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property of 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

There total 10 articles about 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic 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:

methyl 9-hydroxynonanoate (34957-73-8) → 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (203794-79-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / trimethylsilyl triflate / -35 °C

2: 100 percent / NaOMe / methanol

3: 88 percent / PTSA / acetonitrile

4: CH₂Cl₂; dimethylformamide / 16 h / 20 °C

5: 60 percent / NaCNBH₃; HCl; molecular sieves 3A / tetrahydrofuran; diethyl ether

6: 96 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran

7: 93 percent / 2,6-lutidine / dimethylformamide / 16 h / 80 °C

With morpholine; 2,6-dimethylpyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(01)00092-0

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (203794-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / PTSA / acetonitrile

2: CH₂Cl₂; dimethylformamide / 16 h / 20 °C

3: 60 percent / NaCNBH₃; HCl; molecular sieves 3A / tetrahydrofuran; diethyl ether

4: 96 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran

5: 93 percent / 2,6-lutidine / dimethylformamide / 16 h / 80 °C

With morpholine; 2,6-dimethylpyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(01)00092-0

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose (112929-24-5,112929-25-6) → 9-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-3-(3,4-dimethoxy-benzoylamino)-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (203794-79-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / trimethylsilyl triflate / -35 °C

2: 100 percent / NaOMe / methanol

3: 88 percent / PTSA / acetonitrile

4: CH₂Cl₂; dimethylformamide / 16 h / 20 °C

5: 60 percent / NaCNBH₃; HCl; molecular sieves 3A / tetrahydrofuran; diethyl ether

6: 96 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran

7: 93 percent / 2,6-lutidine / dimethylformamide / 16 h / 80 °C

With morpholine; 2,6-dimethylpyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(01)00092-0

upstream raw materials:

methyl 9-hydroxynonanoate

benzaldehyde dimethyl acetal

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose

perbenzyl fucosyl bromide

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