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

Base Information

• Chemical Name: (3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-1-enecarboxylic acid tert-butyl ester
• CAS No.: 212752-24-4
• Molecular Formula: C₂₄H₄₃NO₁₁
• Molecular Weight: 521.606

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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

There total 16 articles about (3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-1-enecarboxylic 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:

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) → (3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-1-enecarboxylic acid tert-butyl ester (212752-24-4)

Guidance literature:

Multi-step reaction with 14 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

8: 92 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

9: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

10: SmI₂, tert-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature

11: 1.) Martin's sulfurane, 2.) AcOH, H₂O / 1.) CCl₄, r.t., 2.) r.t.

12: 82 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

13: 1.) lithium cyclohexyl(isopropyl)amide / 1.) THF, -78 deg C to r.t., 2.) THF, -78 deg C

14: 1.) H₂O₂, 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 2.) r.t.

With pyridine; hydrogenchloride; indium; formic acid; samarium diiodide; Martins sulfurane; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; water; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; lithium cyclohexylisopropylamide; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetonitrile;

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

Reference yield:

tert-butyl 2-(bromomethyl)acrylate (53913-96-5) → (3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-1-enecarboxylic acid tert-butyl ester (212752-24-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

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

3: 92 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

4: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

5: SmI₂, tert-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature

6: 1.) Martin's sulfurane, 2.) AcOH, H₂O / 1.) CCl₄, r.t., 2.) r.t.

7: 82 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

8: 1.) lithium cyclohexyl(isopropyl)amide / 1.) THF, -78 deg C to r.t., 2.) THF, -78 deg C

9: 1.) H₂O₂, 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 2.) r.t.

With pyridine; hydrogenchloride; indium; samarium diiodide; Martins sulfurane; water; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; lithium cyclohexylisopropylamide; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; acetic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; 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-[(3S,4R,5S,6R)-2,5-Dihydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide → (3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-1-enecarboxylic acid tert-butyl ester (212752-24-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

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

3: 92 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

4: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

5: SmI₂, tert-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature

6: 1.) Martin's sulfurane, 2.) AcOH, H₂O / 1.) CCl₄, r.t., 2.) r.t.

7: 82 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

8: 1.) lithium cyclohexyl(isopropyl)amide / 1.) THF, -78 deg C to r.t., 2.) THF, -78 deg C

9: 1.) H₂O₂, 2.) pyridine / 1.) CH₂Cl₂, 0 deg C, 2.) r.t.

With pyridine; hydrogenchloride; indium; samarium diiodide; Martins sulfurane; water; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; lithium cyclohexylisopropylamide; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; acetic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; 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:

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

N-acetyl-β-D-mannosamine

tert-butyl 2-(bromomethyl)acrylate

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

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