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

Base Information

Chemical Name:(1R,4S,5S)-4-Acetylamino-5-methoxymethoxy-3-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-2-enecarboxylic acid tert-butyl ester
CAS No.:212752-21-1
Molecular Formula:C₂₄H₄₃NO₁₁
Molecular Weight:521.606
Hs Code.:

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

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

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

There total 13 articles about (1R,4S,5S)-4-Acetylamino-5-methoxymethoxy-3-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-2-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: 95.0%

: 212752-19-7
(1R,3S,4R,5S)-4-Acetylamino-3-hydroxy-5-methoxymethoxy-3-((1R,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester

: 212752-21-1
(1R,4S,5S)-4-Acetylamino-5-methoxymethoxy-3-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-2-enecarboxylic acid tert-butyl ester

Guidance literature:: With Martins sulfurane; In tetrachloromethane; at 0 ℃;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I

Reference yield:

: 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
N-acetyl-β-D-mannosamine

: 212752-21-1
(1R,4S,5S)-4-Acetylamino-5-methoxymethoxy-3-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-2-enecarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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.

With hydrogenchloride; indium; formic acid; samarium diiodide; Martins sulfurane; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; water; tetra-(n-butyl)ammonium iodide; 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; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; 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-2-(4-methoxy-benzyl)-8-(4-methoxy-benzyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 212752-21-1
(1R,4S,5S)-4-Acetylamino-5-methoxymethoxy-3-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohex-2-enecarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

2: AcOH / Ambient temperature

3: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

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

5: 92 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

6: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

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

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

With hydrogenchloride; indium; formic acid; samarium diiodide; Martins sulfurane; water; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I