(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

Base Information

Chemical Name:(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester
CAS No.:612065-82-4
Molecular Formula:C₂₃H₂₉NO₈S
Molecular Weight:479.551
Hs Code.:

Synonyms:(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

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Chemical Property of (2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

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Technology Process of (2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

There total 7 articles about (2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic 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: 83.0%

: 98-59-9
p-toluenesulfonyl chloride

: 612065-57-3
(2S,3R)-5-Benzyloxycarbonylamino-2,3-dihydroxy-3-methyl-pentanoic acid ethyl ester

: 612065-82-4
(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

Guidance literature:: With triethylamine; In dichloromethane;

Reference yield:

: 65564-05-8
3-[(benzyloxycarbonyl)amino]propanal

: 612065-82-4
(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / tetrahydrofuran / -78 °C

2.1: 85 percent / (COCl)2; DMSO / CH₂Cl₂ / -60 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: 78 percent / tetrahydrofuran / 20 °C

4.1: 94 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C

5.1: 83 percent / Et₃N / CH₂Cl₂

With oxalyl dichloride; methanesulfonamide; AD-mix-β; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2.1: Swern oxidation / 3.2: Wittig-Horner reaction / 4.1: Sharpless asymmetric dihydroxylation;

Reference yield:

: 34637-22-4
3-[(N-benzyloxycarbonyl)amino]propanol

: 612065-82-4
(2S,3R)-5-Benzyloxycarbonylamino-3-hydroxy-3-methyl-2-(toluene-4-sulfonyloxy)-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 83 percent / (COCl)2; DMSO / CH₂Cl₂ / -60 °C

2.1: 77 percent / tetrahydrofuran / -78 °C

3.1: 85 percent / (COCl)2; DMSO / CH₂Cl₂ / -60 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

4.2: 78 percent / tetrahydrofuran / 20 °C

5.1: 94 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C

6.1: 83 percent / Et₃N / CH₂Cl₂

With oxalyl dichloride; methanesulfonamide; AD-mix-β; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1.1: Swern oxidation / 3.1: Swern oxidation / 4.2: Wittig-Horner reaction / 5.1: Sharpless asymmetric dihydroxylation;