(2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol

Base Information

• Chemical Name: (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol
• CAS No.: 1027918-84-8
• Molecular Formula: C₄₁H₆₄O₈
• Molecular Weight: 684.954
• Mol file: 1027918-84-8.mol

Synonyms:

Chemical Property of (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol

There total 31 articles about (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol 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:

(4S,5R,6R)-4-[(1S,4R,5R,6S,7S,8R,9S,10S)-10-Benzyloxy-8-(4-methoxy-benzyloxy)-1,5,7,9-tetramethyl-3-methylene-4,6-bis-triethylsilanyloxy-undecyl]-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxane → (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol (1027918-84-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 10h;

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) → (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol (1027918-84-8)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 18-crown-6 ether; 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; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; benzene; 15.1: Wittig reaction;

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) → (2S,5R,6R,7R,8R,9S,10S,11S)-11-Benzyloxy-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-4-methylene-dodecane-5,7-diol (1027918-84-8)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; dmap; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; butanone; pentane; 7.1: Wittig reaction;

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

upstream raw materials:

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

(S)-2-[(4R,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propan-1-ol

Downstream raw materials:

(S)-2-((4R,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-[(1S,2R,3S,4S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-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)-propan-1-ol

(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

C₄₂H₅₈O₉

(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