(3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione

Base Information

• Chemical Name: (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione
• CAS No.: 1335287-14-3
• Molecular Formula: C₂₇H₃₇NO₉
• Molecular Weight: 519.592
• Mol file: 1335287-14-3.mol

Synonyms:(3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione

Chemical Property of (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione

There total 15 articles about (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione 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: 63.0%

(1S,2R,3E)-4-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-(acryloylbenzylamino)-butenoate (1335287-13-2) → (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione (1335287-14-3)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

ethyl (2E,4S,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-2-hexenoate → (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione (1335287-14-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: triphenylphosphine; diethylazodicarboxylate / toluene; benzene / 2 h / 0 - 20 °C / Inert atmosphere

2.1: methanol; ammonia / water / 3 h / 0 - 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydroxide / tetrahydrofuran; methanol; water / 2 h / 0 - 20 °C

4.2: pH 3 - 4

5.1: triethylamine / toluene / 0.5 h / 0 °C / Inert atmosphere

6.1: dmap / toluene / 1 h / 20 °C / Inert atmosphere

7.1: water; acetic acid / tetrahydrofuran / Inert atmosphere

8.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere

9.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

9.2: Inert atmosphere; Saturated solution

10.1: 2-picoline borane complex; acetic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere

13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; dmap; 2-picoline borane complex; tetrabutyl ammonium fluoride; ammonia; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 6.1: Yamaguchi reaction;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

(1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate (1335287-11-0) → (3S,6E,8R,9S,12E,14R,15S)-4-benzyl-8-hydroxy-14-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-4-aza-10,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione (1335287-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.08.014

upstream raw materials:

(1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate

(1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-(acryloylbenzylamino)-butenoate

(1S,2R,3E)-4-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-(acryloylbenzylamino)-butenoate

(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl (2E,4R,5S)-5-tert-butyldimethylsilyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate

Downstream raw materials:

C₂₃H₂₉NO₇

C₂₃H₂₅NO₇