5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

Base Information

Chemical Name:5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester
CAS No.:935696-77-8
Molecular Formula:C₃₂H₅₅NO₈S
Molecular Weight:613.857
Hs Code.:

5-<i>tert</i>-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

Synonyms:5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

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Chemical Property of 5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

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Technology Process of 5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

There total 6 articles about 5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic 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: 70.0%

: 935696-73-4
5-tert-butoxycarbonylamino-2,3-dihydroxy-octadecanoic acid ethyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 935696-77-8
5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 12h;
DOI:10.1016/j.tetlet.2007.01.143

Reference yield:

: 894086-03-4
(S)-4-hydroxy-1-heptadecane

: 935696-77-8
5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 71 percent / diphenylphosphoryl azide; TPP; DEAD / tetrahydrofuran / 12 h / 0 °C

2.1: 68 percent / TPP / tetrahydrofuran; H₂O / 24 h / 20 °C

3.1: O₂; DMS / -78 °C

3.2: 76 percent / benzene / 3 h / 20 °C

4.1: AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

5.1: 70 percent / DIPEA / CH₂Cl₂ / 12 h / 0 °C

With 2,3-dimercapto-succinic acid; methanesulfonamide; diphenylphosphoranyl azide; oxygen; thiamine diphosphate; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1.1: Mitsunobu inversion reaction / 3.2: Wittig olefination reaction / 4.1: Sharpless asymmetric dihydroxylation reaction;
DOI:10.1016/j.tetlet.2007.01.143

Reference yield:

: 935696-74-5
4-azido-heptadec-1-ene

: 935696-77-8
5-tert-butoxycarbonylamino-3-hydroxy-2-(toluene-4-sulfonyloxy)-octadecanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 68 percent / TPP / tetrahydrofuran; H₂O / 24 h / 20 °C

2.1: O₂; DMS / -78 °C

2.2: 76 percent / benzene / 3 h / 20 °C

3.1: AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

4.1: 70 percent / DIPEA / CH₂Cl₂ / 12 h / 0 °C

With 2,3-dimercapto-succinic acid; methanesulfonamide; oxygen; thiamine diphosphate; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2.2: Wittig olefination reaction / 3.1: Sharpless asymmetric dihydroxylation reaction;
DOI:10.1016/j.tetlet.2007.01.143