(2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester

Base Information

• Chemical Name: (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester
• CAS No.: 124288-99-9
• Molecular Formula: C₃₂H₄₅NO₁₁S₂
• Molecular Weight: 683.841

Synonyms:(2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester

Chemical Property of (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester

There total 10 articles about (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic 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: 63.0%

p-toluenesulfonylanhydride (4124-41-8) + tert-Butyl -β-D-allo-decofuranosid>uronate (124288-82-0,124288-98-8) → 1,1-dimethylethyl -9(S)-<<(4-methylphenyl)sulfonyl>amino>-2,3-O-(1-methylethylidene)-β-D-allo-decofuranosid>uronate (124288-83-1) + (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester (124288-99-9)

Guidance literature:

With pyridine; at 0 ℃; for 0.666667h;

DOI:10.1021/jo00290a028

Reference yield:

α-N-tosyl-δ-N-carbobenzoxyornthine (110414-90-9) → (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester (124288-99-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / CHCl₃ / 22 h / 22 °C

2: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

3: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

4: 86 percent / KF / acetonitrile / 24 h / 22 °C

5: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

6: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

7: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

8: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

9: pyridine / 1 h / 0 °C

With pyridine; potassium fluoride; ammonium cerium(IV) nitrate; hydrogen; nitric acid; L-Selectride; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00290a028

Reference yield:

1,1-dimethylethyl (S)-2-<<(4-methylphenyl)sulfonyl>-amino>-5-<<(phenylmethoxy)carbonyl>amino>pentanoate (124288-73-9) → (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester (124288-99-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

2: 56 percent / m-CPBA / CH₂Cl₂ / 0.28 h / Heating

3: 86 percent / KF / acetonitrile / 24 h / 22 °C

4: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C

5: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C

6: 81 percent / cerium(IV) ammonium nitrate, HNO₃ / ethanol / 0.25 h / -42 °C

7: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

8: pyridine / 1 h / 0 °C

With pyridine; potassium fluoride; ammonium cerium(IV) nitrate; hydrogen; nitric acid; L-Selectride; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00290a028

upstream raw materials:

p-toluenesulfonylanhydride

tert-Butyl -β-D-allo-decofuranosid>uronate

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

1,1-dimethylethyl (S)-5-amino-2-<<(4-methylphenyl)sulfonyl>-amino>pentanoate

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