(2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol

Base Information

• Chemical Name: (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol
• CAS No.: 549505-02-4
• Molecular Formula: C₅₀H₇₀O₇SSi₂
• Molecular Weight: 871.339

Synonyms:(2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol

Chemical Property of (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol

There total 10 articles about (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-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: 80.0%

Triethyl-[(R)-2-(4-methoxy-benzyloxy)-1-(R)-oxiranyl-ethoxy]-silane + ((3S,4S)-4-Benzyloxy-3-methylsulfanylmethoxy-hept-6-ynyloxy)-tert-butyl-diphenyl-silane (549504-97-4) → (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol (549505-02-4)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(03)00432-5

Reference yield:

5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one (106183-57-7) → (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol (549505-02-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 81 percent / Ac₂O / acetic acid / 70 °C

2: 87 percent / LiBH₄ / diethyl ether

3: imidazole / dimethylformamide

4: pyridine; DMAP / CH₂Cl₂

5: 78 percent / 1N HCl / methanol; tetrahydrofuran

6: 86 percent / K₂CO₃ / methanol; CH₂Cl₂

7: 51 percent / dimethylsulfoxide; tetrahydrofuran

8: 97 percent / NaH; Bu₄NI / tetrahydrofuran

9: 80 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; n-butyllithium; boron trifluoride diethyl etherate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; 9: Yamaguchi method;

DOI:10.1016/S0040-4039(03)00432-5

Reference yield:

2-deoxy-D-ribonolactone (34371-14-7) → (2R,3R,8S,9S)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-9-methylsulfanylmethoxy-2-triethylsilanyloxy-undec-5-yn-3-ol (549505-02-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 70 percent / AgNO₃; pyridine / acetonitrile

2: 81 percent / Ac₂O / acetic acid / 70 °C

3: 87 percent / LiBH₄ / diethyl ether

4: imidazole / dimethylformamide

5: pyridine; DMAP / CH₂Cl₂

6: 78 percent / 1N HCl / methanol; tetrahydrofuran

7: 86 percent / K₂CO₃ / methanol; CH₂Cl₂

8: 51 percent / dimethylsulfoxide; tetrahydrofuran

9: 97 percent / NaH; Bu₄NI / tetrahydrofuran

10: 80 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; n-butyllithium; boron trifluoride diethyl etherate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; silver nitrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 10: Yamaguchi method;

DOI:10.1016/S0040-4039(03)00432-5

upstream raw materials:

((3S,4S)-4-Benzyloxy-3-methylsulfanylmethoxy-hept-6-ynyloxy)-tert-butyl-diphenyl-silane

5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one

2-deoxy-D-ribonolactone

(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylsulfanylmethoxy-dihydro-furan-2-one

Downstream raw materials:

Methanesulfonic acid (1R,6S,7S)-6-benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-1-[(R)-2-(4-methoxy-benzyloxy)-1-triethylsilanyloxy-ethyl]-7-methylsulfanylmethoxy-non-3-ynyl ester

Methanesulfonic acid (1R,6S,7S)-6-benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-1-[(R)-1-hydroxy-2-(4-methoxy-benzyloxy)-ethyl]-7-methylsulfanylmethoxy-non-3-ynyl ester

{(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane

(3S,4S)-4-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-yn-3-ol

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