(5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol

Base Information

• Chemical Name: (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol
• CAS No.: 158587-51-0
• Molecular Formula: C₃₂H₆₀O₄Si₂
• Molecular Weight: 564.997

Synonyms:(5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol

Chemical Property of (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol

There total 12 articles about (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-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: 91.0%

(6S,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-one (158587-50-9) → (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol (158587-51-0)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; 1.) -78 deg C, 30 min; 2.) r.t., 1.5 h;

DOI:10.1016/S0040-4039(00)78234-7

Reference yield:

4-benzyloxybutanal (5470-84-8) → (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol (158587-51-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) freshly distilled di-n-butylboron triflate; 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) CH₂Cl₂, -78 to 0 deg C, 1 h; 3.) CH₂Cl₂, -78 to 0 deg C, 1 h

2: 48percent aq. HF / acetonitrile / 0.33 h / Ambient temperature

3: sat aq. NaHCO₃, K₂CO₃ / acetonitrile; H₂O / 2 h

4: 97 percent / collidine / CH₂Cl₂ / -78 deg C to r.t.

5: t-butyllithium / diethyl ether / 1.5 h / -100 - -78 °C

6: collidine / diethyl ether / 2.5 h / -78 deg C to r.t.

7: 91 percent / LiEt₃BH / tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) r.t., 1.5 h

With 2,3,5-trimethyl-pyridine; hydrogen fluoride; tert.-butyl lithium; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)78234-7

Reference yield:

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal (123444-68-8) → (5R,6R,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-ol (158587-51-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1 M KMnO₄, 0.5 M NaH₂PO₄ / 2-methyl-propan-2-ol / 0.25 h

2: triethylamine / tetrahydrofuran / 0.5 h / 0 deg C to r.t.

3: n-butyllithium / tetrahydrofuran / 2 h / -78 deg C to r.t.

4: 1.) freshly distilled di-n-butylboron triflate; 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) CH₂Cl₂, -78 to 0 deg C, 1 h; 3.) CH₂Cl₂, -78 to 0 deg C, 1 h

5: 48percent aq. HF / acetonitrile / 0.33 h / Ambient temperature

6: sat aq. NaHCO₃, K₂CO₃ / acetonitrile; H₂O / 2 h

7: 97 percent / collidine / CH₂Cl₂ / -78 deg C to r.t.

8: t-butyllithium / diethyl ether / 1.5 h / -100 - -78 °C

9: collidine / diethyl ether / 2.5 h / -78 deg C to r.t.

10: 91 percent / LiEt₃BH / tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) r.t., 1.5 h

With 2,3,5-trimethyl-pyridine; potassium permanganate; sodium dihydrogenphosphate; n-butyllithium; hydrogen fluoride; tert.-butyl lithium; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)78234-7

upstream raw materials:

(6S,7R)-10-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-1-en-5-one

4-benzyloxybutanal

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

(3S)-4-[(tert-butyldiphenylsilyl)oxy]-3-methylbutanenitrile

Downstream raw materials:

Methanesulfonic acid (1R,2S,3R)-6-benzyloxy-1-but-3-enyl-3-(tert-butyl-dimethyl-silanyloxy)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-hexyl ester

(1S,3aR,10aS,10bR)-1-methyloctahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione

(S)-5-{(1R,2R)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pentyl}-pyrrolidin-2-one

{(4R,5R,6S)-6-Azido-4-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-dec-9-enyloxymethyl}-benzene

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