2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

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Chemical Name:2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate
CAS No.:913288-81-0
Molecular Formula:C₃₂H₄₁NO₄S₂
Molecular Weight:567.814
Hs Code.:

Synonyms:2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

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Chemical Property of 2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

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Technology Process of 2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

There total 9 articles about 2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate 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: 94.0%

: 913288-78-5
(1'S,2'R)-2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl thiolpropionate

: 78-84-2
isobutyraldehyde

: 2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2R,2'R,3R)-2,4-dimethyl-3-hydroxy-thiolpentanoate

: 913288-81-0
2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

Guidance literature:: With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 - 0 ℃; for 3h;
DOI:10.1021/ol0614774

Reference yield:

: 37577-28-9,58550-13-3,757124-50-8
(1S,2R)-(+)-norphedrine

: 913288-81-0
2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 87 percent / methanesulfonylchloride; Et₃N / 14.17 h / 0 - 20 °C

3: 93 percent / PBu₃ / acetonitrile; H₂O / 18 h / 20 °C

4: NaH / dimethylformamide / 18 h / 20 °C

5: 96 percent / NaOMe / methanol / 1.5 h / 20 °C

6: 83 percent / pyridine / CH₂Cl₂ / 18 h / 0 - 20 °C

7: 94 percent / dicyclohexylboron triflate; Et₃N / CH₂Cl₂; hexane / 3 h / -78 - 0 °C

With pyridine; tributylphosphine; sodium methylate; sodium hydride; methanesulfonyl chloride; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol0614774

Reference yield:

: 773-64-8
2-mesitylenesulphonyl chloride

: 913288-81-0
2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl (1'S,2S,2'R,3S)-2,4-dimethyl-3-hydroxy-thiolpentanoate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 87 percent / methanesulfonylchloride; Et₃N / 14.17 h / 0 - 20 °C

3: 93 percent / PBu₃ / acetonitrile; H₂O / 18 h / 20 °C

4: NaH / dimethylformamide / 18 h / 20 °C

5: 96 percent / NaOMe / methanol / 1.5 h / 20 °C

6: 83 percent / pyridine / CH₂Cl₂ / 18 h / 0 - 20 °C

7: 94 percent / dicyclohexylboron triflate; Et₃N / CH₂Cl₂; hexane / 3 h / -78 - 0 °C

With pyridine; tributylphosphine; sodium methylate; sodium hydride; methanesulfonyl chloride; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol0614774