(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

Base Information

Chemical Name:(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione
CAS No.:1026655-91-3
Molecular Formula:C₂₅H₃₉NO₄
Molecular Weight:417.589
Hs Code.:

Synonyms:(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

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Chemical Property of (3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

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Technology Process of (3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

There total 18 articles about (3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione 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:

: 2121-69-9,54630-82-9,107173-22-8,3817-48-9
(2R,4S)-2,4-dimethylpentane-1,5-diol

: 1026655-91-3
(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

Guidance literature:: Multi-step reaction with 11 steps

1: 83 percent / lipase PS-30 / 1,2-dimethoxy-ethane / 23 °C

2: imidazole

3: DIBAL / -78 °C

4: SO₃*pyridine; Et₃N; DMSO / 0 °C

5: n-BuLi / tetrahydrofuran

6: nBu₄NF / tetrahydrofuran

7: PDC / dimethylformamide

8: EDCI; HOBt / 23 °C

9: 93 percent / second-generation Grubbs' catalyst / CH₂Cl₂ / 42 °C

10: nBu₄NF

11: H₂ / Pd(OH)2 / methanol

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; lipase PS-30; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 5: Wittig reaction;
DOI:10.1021/ol049292p

Reference yield:

: 116179-61-4
(2R,4R)-2,4-dimethyl-hex-5-enoic acid

: 1026655-91-3
(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

Guidance literature:: Multi-step reaction with 4 steps

1: EDCI; HOBt / 23 °C

2: 93 percent / second-generation Grubbs' catalyst / CH₂Cl₂ / 42 °C

3: nBu₄NF

4: H₂ / Pd(OH)2 / methanol

With tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium dihydroxide; In methanol; dichloromethane;
DOI:10.1021/ol049292p

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 1026655-91-3
(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 73 percent / PPh₃; DEAD / diethyl ether / 23 °C

2: trifluoroacetic acid / 0 °C

3: EDCI; HOBt / 23 °C

4: 93 percent / second-generation Grubbs' catalyst / CH₂Cl₂ / 42 °C

5: nBu₄NF

6: H₂ / Pd(OH)2 / methanol

With tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; 2: Mitsunobu esterification;
DOI:10.1021/ol049292p