(2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol

Base Information

• Chemical Name: (2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol
• CAS No.: 565226-32-6
• Molecular Formula: C₆₈H₁₁₀O₉Si₃
• Molecular Weight: 1155.87
• Mol file: 565226-32-6.mol

Synonyms:(2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol

Chemical Property of (2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol

There total 27 articles about (2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-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: 78.0%

(2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane (251099-27-1) + (2R,3R,4S,5S,6R,7S,8S)-8-Benzyloxy-6-(4-methoxy-benzyloxy)-3,5,7-trimethyl-2,4-bis-triethylsilanyloxy-nonanal (565226-26-8) → (2S,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol (565226-32-6)

Guidance literature:

(2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; for 1h;

(2R,3R,4S,5S,6R,7S,8S)-8-Benzyloxy-6-(4-methoxy-benzyloxy)-3,5,7-trimethyl-2,4-bis-triethylsilanyloxy-nonanal; In diethyl ether; pentane; at -78 ℃; for 1.5h;

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,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol (565226-32-6)

Guidance literature:

Multi-step reaction with 13 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

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; hydrogen; tert.-butyl lithium; potassium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide; Raney Ni (W-2); In diethyl ether; ethanol; dichloromethane; water; acetone; butanone; pentane; benzene;

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,4S,5R,6R,7S,8S,9R,10S,11S)-11-Benzyloxy-2-{(4S,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-9-(4-methoxy-benzyloxy)-6,8,10-trimethyl-5,7-bis-triethylsilanyloxy-dodecan-4-ol (565226-32-6)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 1H-imidazole; dmap; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; sodium iodide; Raney Ni (W-2); In diethyl ether; ethanol; dichloromethane; butanone; pentane;

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

upstream raw materials:

(2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane

(2R,3R,4S,5S,6R,7S,8S)-8-Benzyloxy-6-(4-methoxy-benzyloxy)-3,5,7-trimethyl-2,4-bis-triethylsilanyloxy-nonanal

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

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

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

Refernces