(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

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Chemical Name:(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol
CAS No.:205517-82-4
Molecular Formula:C₃₃H₄₉NO₅S
Molecular Weight:571.822
Hs Code.:

Synonyms:(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

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Chemical Property of (3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

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Technology Process of (3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

There total 14 articles about (3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol 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: 92.0%

: 205517-81-3
(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

: 205517-82-4
(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.3987/COM-97-S(N)24

Reference yield:

: 922-65-6
divinylcarbinol

: 205517-82-4
(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 65 percent / TBHP, L-(+)-DIPT, Ti(O-iso-Pr)4, 4 Angstroem molecular sieves / CH₂Cl₂ / 240 h / -20 °C

2: 80 percent / NaH, n-Bu₄NI / tetrahydrofuran / -10 °C

3: 76 percent / CuI / tetrahydrofuran / -50 °C

4: NEt₃ / CH₂Cl₂ / 4 h / Ambient temperature

5: sodium azide / dimethylformamide / 5 h / 90 °C

6: LiAlH₄ / tetrahydrofuran / Ambient temperature

7: NEt₃ / CH₂Cl₂ / Ambient temperature

8: 84 percent / DHQD-CLB, K₃, K₂CO₃, OsO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

9: 94 percent / imidazole / dimethylformamide / 5 h / 0 °C

10: 92 percent / PPh₃, DEAD / tetrahydrofuran / 0 °C

11: 81 percent / MgBr₂ / diethyl ether / 3 h / Ambient temperature

12: 89 percent / 1.) oxalyl chloride, DMSO; 2.) NEt₃ / CH₂Cl₂ / -78 °C

13: 88 percent / 4 Angstroem molecular sieves / toluene / 3 h / -78 °C

14: 92 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 10,11-dihydroquinidine p-chlorobenzoate; dimethyl sulfoxide; triethylamine; triphenylphosphine; magnesium bromide; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/COM-97-S(N)24

Reference yield:

: 100017-22-9
(S)-1-[(R)-oxiran-2-yl]prop-2-enol

: 205517-82-4
(3S,4S)-14-[(2S,3R,4R)-3-Benzyloxy-4-hydroxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-3-methyl-tetradec-1-en-4-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 80 percent / NaH, n-Bu₄NI / tetrahydrofuran / -10 °C

2: 76 percent / CuI / tetrahydrofuran / -50 °C

3: NEt₃ / CH₂Cl₂ / 4 h / Ambient temperature

4: sodium azide / dimethylformamide / 5 h / 90 °C

5: LiAlH₄ / tetrahydrofuran / Ambient temperature

6: NEt₃ / CH₂Cl₂ / Ambient temperature

7: 84 percent / DHQD-CLB, K₃, K₂CO₃, OsO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

8: 94 percent / imidazole / dimethylformamide / 5 h / 0 °C

9: 92 percent / PPh₃, DEAD / tetrahydrofuran / 0 °C

10: 81 percent / MgBr₂ / diethyl ether / 3 h / Ambient temperature

11: 89 percent / 1.) oxalyl chloride, DMSO; 2.) NEt₃ / CH₂Cl₂ / -78 °C

12: 88 percent / 4 Angstroem molecular sieves / toluene / 3 h / -78 °C

13: 92 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With 1H-imidazole; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 10,11-dihydroquinidine p-chlorobenzoate; dimethyl sulfoxide; triethylamine; triphenylphosphine; magnesium bromide; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/COM-97-S(N)24