(2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

Base Information

Chemical Name:(2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester
CAS No.:444309-27-7
Molecular Formula:C₁₄H₂₀O₆S
Molecular Weight:316.375
Hs Code.:

Synonyms:(2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

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Chemical Property of (2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

Chemical Property:

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Technology Process of (2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

There total 2 articles about (2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl 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:

: 98-59-9
p-toluenesulfonyl chloride

: (S)-3,4-Dihydroxy-2-methyl-butyric acid ethyl ester

: 444309-27-7
(2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1002/1521-3765(20020402)8:7<1670::AID-CHEM1670>3.0.CO;2-4

Reference yield:

: diethyl 2(S)-hydroxy-3-methylsuccinate

: 444309-27-7
(2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 0.25 h / 20 °C

1.2: NaBH₄ / tetrahydrofuran / 20 °C

2.1: 5.24 g / dibutyltin oxide; Et₃N / CH₂Cl₂ / 20 °C

With dimethylsulfide borane complex; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1521-3765(20020402)8:7<1670::AID-CHEM1670>3.0.CO;2-4

Reference yield:

: 444309-27-7
(2R,3S)-3-hydroxy-2-methyl-4-(toluene-4-sulfonyloxy)butyric acid ethyl ester

: (2R,3S)-3-Hydroxy-N-{3-[(2R,3S,6S,8S)-8-((E)-(R)-6-hydroxy-3,5-dimethyl-hept-4-enyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-propyl}-4-{2-[(2R,3R,6S)-6-((E)-2-hydroxy-pent-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-acetylamino}-2-methyl-butyramide

Guidance literature:: Multi-step reaction with 9 steps

1: 74 percent / NaN₃ / dimethylformamide / 4 h / 70 °C

2: 87 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

3: 50.3 mg / aq. LiOH / ethanol / 48 h / 20 °C

4: 80 percent / Et₃N / tetrahydrofuran; dimethylformamide / 0.25 h / 0 °C

5: H₂ / 10 percent Pd/C / tetrahydrofuran / 4.5 h / 20 °C

6: 2.8 mg / PyBOP; Et₃N / CH₂Cl₂ / 19 h

7: 100 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

8: PyBOP; (iPr)2NEt / dimethylformamide / 27 h / 20 °C

9: PPTS / methanol / 20 h / 20 °C

With 1H-imidazole; lithium hydroxide; sodium azide; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; pyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/1521-3765(20020402)8:7<1670::AID-CHEM1670>3.0.CO;2-4