(1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

Base Information

• Chemical Name: (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one
• CAS No.: 565226-34-8
• Molecular Formula: C₄₃H₆₂O₇
• Molecular Weight: 690.961
• Mol file: 565226-34-8.mol

Synonyms:

Chemical Property of (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

There total 39 articles about (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one 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:

(R)-2-((4S,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-((1S,2R,3R,4S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-pentyl)-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid (565226-25-7) → (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (565226-34-8)

Guidance literature:

(R)-2-((4S,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-((1S,2R,3R,4S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-pentyl)-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 20h;

With dmap; In tetrahydrofuran; toluene; for 20h; Heating;

DOI:10.1016/S0040-4039(03)00955-9

Reference yield:

1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol (106357-30-6) → (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (565226-34-8)

Guidance literature:

Multi-step reaction with 24 steps

1.1: 73 percent / KH; 18-crown-6 / 3 h / 25 °C

2.1: OsO₄; NMO / acetone; H₂O / 20 h / 25 °C

3.1: NaIO₄ / acetone; H₂O / 20 h / 25 °C

4.1: BF₃*OEt₂ / CH₂Cl₂ / 6 h / -90 - -30 °C

5.1: TsOH / benzene / 14 h / 25 °C

6.1: OsO₄; NMO / acetone; H₂O / 20 h / 25 °C

7.1: NaIO₄ / acetone; H₂O / 1 h / 20 °C

8.1: LiAlH₄ / diethyl ether / 0.25 h / 0 °C

9.1: imidazole / CH₂Cl₂ / 1 h / 25 °C

10.1: H₂ / Raney Ni (W-2) / ethanol / 120 h / 25 °C

11.1: pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

12.1: NaI; NaHCO₃ / butan-2-one / 20 h / 60 °C

13.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C

13.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

15.1: t-BuOK / toluene / 1.5 h / 95 °C

16.1: TBAF / tetrahydrofuran / 10 h / 20 °C

17.1: imidazole / CH₂Cl₂ / 0.25 h / 20 °C

18.1: CSA / CH₂Cl₂ / 1 h / 15 °C

19.1: TBAF / tetrahydrofuran / 3 h / 20 °C

20.1: Jones reagent / acetone / 1.5 h / -30 °C

21.1: diethyl ether / 0.5 h / 0 °C

22.1: DDQ / CH₂Cl₂; H₂O / 0.25 h / 0 °C

23.1: NaOH / methanol / 90 h / 20 °C

24.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 h / 20 °C

24.2: 22 percent Turnov_. / DMAP / tetrahydrofuran; toluene / 20 h / Heating

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; jones reagent; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; benzene; 15.1: Wittig reaction / 20.1: Jones oxidation;

DOI:10.1016/S0040-4039(03)00955-9

Reference yield:

(S)-2-[(4R,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propan-1-ol (97718-92-8) → (1R,4S,5S,9S,10R,13R,14R,15S,17S,19R,20R)-13-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-4,7,7,10,14,19,20-heptamethyl-2-methylene-17-(2,4,6-trimethyl-phenyl)-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (565226-34-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: imidazole / CH₂Cl₂ / 1 h / 25 °C

2.1: H₂ / Raney Ni (W-2) / ethanol / 120 h / 25 °C

3.1: pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

4.1: NaI; NaHCO₃ / butan-2-one / 20 h / 60 °C

5.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C

5.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: t-BuOK / toluene / 1.5 h / 95 °C

8.1: TBAF / tetrahydrofuran / 10 h / 20 °C

9.1: imidazole / CH₂Cl₂ / 0.25 h / 20 °C

10.1: CSA / CH₂Cl₂ / 1 h / 15 °C

11.1: TBAF / tetrahydrofuran / 3 h / 20 °C

12.1: Jones reagent / acetone / 1.5 h / -30 °C

13.1: diethyl ether / 0.5 h / 0 °C

14.1: DDQ / CH₂Cl₂; H₂O / 0.25 h / 0 °C

15.1: NaOH / methanol / 90 h / 20 °C

16.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 h / 20 °C

16.2: 22 percent Turnov_. / DMAP / tetrahydrofuran; toluene / 20 h / Heating

With pyridine; 1H-imidazole; dmap; sodium hydroxide; jones reagent; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; 7.1: Wittig reaction / 12.1: Jones oxidation;

DOI:10.1016/S0040-4039(03)00955-9

upstream raw materials:

(R)-2-((4S,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-((1S,2R,3R,4S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-pentyl)-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid

1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

(2RS,3SR)-3-O-benzyl-2-methyl-1,3-butanediol

(2R,3S)-1-Benzyloxymethyloxy-2-methylbutan-3-ol

Downstream raw materials:

(1S,2R,5S,6R,7R,8R,9R,12S,13S,15S,17R)-5-((1S,2S)-2-Benzyloxy-1-methyl-propyl)-7,9-dihydroxy-2,6,8,12,17-pentamethyl-10-methylene-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

C₄₀H₅₈O₈

C₄₂H₅₈O₉

Refernces