(4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester
• CAS No.: 212752-15-3
• Molecular Formula: C₃₂H₅₃NO₁₃
• Molecular Weight: 659.772

Synonyms:(4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester

Chemical Property of (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester

There total 8 articles about (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl 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: 91.0%

chloromethyl methyl ether (107-30-2) + (4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester (212752-13-1) → (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester (212752-15-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; 4-pyrrolidin-1-ylpyridine; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 0 - 25 ℃;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I

Reference yield:

N-acetyl-β-D-mannosamine (72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester (212752-15-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / BF₃*Et₂O / 95 °C

2: 70 percent / p-TsOH / acetonitrile / 0 °C

3: 88 percent / CF₃SO₃H / tetrahydrofuran; diethyl ether / 0 °C

4: HCO₂H, Et₃N / Pd(PPh₃)4 / dioxane / 65 - 95 °C

5: AcOH / Ambient temperature

6: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

7: 91 percent / (i-Pr)2NEt, TBAI, 4-pyrrolidinylpyridine / 1,2-dichloro-ethane / 0 - 25 °C

With hydrogenchloride; indium; formic acid; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; water; tetra-(n-butyl)ammonium iodide; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I

Reference yield:

N-[(4aR,7S,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-benzyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide → (4S,5R,6R,7S,8R)-5-Acetylamino-6-(4-methoxy-benzyloxy)-4,7,8,9-tetrakis-methoxymethoxy-2-methylene-nonanoic acid tert-butyl ester (212752-15-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / CF₃SO₃H / tetrahydrofuran; diethyl ether / 0 °C

2: HCO₂H, Et₃N / Pd(PPh₃)4 / dioxane / 65 - 95 °C

3: AcOH / Ambient temperature

4: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

5: 91 percent / (i-Pr)2NEt, TBAI, 4-pyrrolidinylpyridine / 1,2-dichloro-ethane / 0 - 25 °C

With hydrogenchloride; indium; formic acid; trifluorormethanesulfonic acid; water; tetra-(n-butyl)ammonium iodide; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I

upstream raw materials:

chloromethyl methyl ether

(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

N-acetyl-β-D-mannosamine

tert-butyl 2-(bromomethyl)acrylate

Downstream raw materials:

(1R,3S,4R,5S)-4-Acetylamino-3-hydroxy-5-methoxymethoxy-3-((1R,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester

(1S,3R,4R,5S)-4-Acetylamino-3-hydroxy-5-methoxymethoxy-3-((1R,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester

(1R,4S,5S)-4-Acetylamino-5-methoxymethoxy-3-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-2-enecarboxylic acid tert-butyl ester

(1S,3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-1-phenylselanyl-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester

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