(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal

Base Information

• Chemical Name: (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal
• CAS No.: 158587-53-2
• Molecular Formula: C₃₁H₅₇N₃O₄Si₂
• Molecular Weight: 591.982

Synonyms:(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal

Chemical Property of (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal

There total 15 articles about (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal 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:

4-benzyloxybutanal (5470-84-8) → (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal (158587-53-2)

Guidance literature:

Multi-step reaction with 10 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

8: 96 percent / pyridine / 12 h / Ambient temperature

9: NaN₃ / hexamethylphosphoric acid triamide / 9 h / Ambient temperature

10: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂/CH₃OH, -78 deg C; 2.) CH₂Cl₂/CH₃OH -78 deg C to r.t., 3 h

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

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

Reference yield:

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal (123444-68-8) → (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal (158587-53-2)

Guidance literature:

Multi-step reaction with 13 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

11: 96 percent / pyridine / 12 h / Ambient temperature

12: NaN₃ / hexamethylphosphoric acid triamide / 9 h / Ambient temperature

13: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂/CH₃OH, -78 deg C; 2.) CH₂Cl₂/CH₃OH -78 deg C to r.t., 3 h

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

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

Reference yield:

(3S)-4-[(tert-butyldiphenylsilyl)oxy]-3-methylbutanenitrile (136262-53-8) → (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanal (158587-53-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) i-Bu₂AlH; 2.) H₃O⁽¹⁺⁾ / 1.) diethyl ether, -78 deg C to r.t., 1.5 h

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

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

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

5: 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

6: 48percent aq. HF / acetonitrile / 0.33 h / Ambient temperature

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

8: 97 percent / collidine / CH₂Cl₂ / -78 deg C to r.t.

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

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

11: 91 percent / LiEt₃BH / tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) r.t., 1.5 h

12: 96 percent / pyridine / 12 h / Ambient temperature

13: NaN₃ / hexamethylphosphoric acid triamide / 9 h / Ambient temperature

14: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂/CH₃OH, -78 deg C; 2.) CH₂Cl₂/CH₃OH -78 deg C to r.t., 3 h

With pyridine; 2,3,5-trimethyl-pyridine; potassium permanganate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; dimethylsulfide; hydrogen fluoride; oxonium; tert.-butyl lithium; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol;

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

upstream raw materials:

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

4-benzyloxybutanal

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

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

Downstream raw materials:

(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanoic acid methyl ester

(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

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

(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanoic acid

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