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

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]-nonanoic acid
CAS No.:158587-54-3
Molecular Formula:C₃₁H₅₇N₃O₅Si₂
Molecular Weight:607.982
Hs Code.:

Synonyms:(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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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]-nonanoic acid

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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]-nonanoic acid

There total 16 articles about (4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanoic acid 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:

: 5470-84-8
4-benzyloxybutanal

: 158587-54-3
(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanoic acid

Guidance literature:: Multi-step reaction with 11 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

11: NaClO₂, NaH₂PO₄*H₂O / acetonitrile; 2-methyl-propan-2-ol; H₂O; various solvent(s) / 0.5 h / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; sodium chlorite; sodium dihydrogenphosphate; 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:

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

: 158587-54-3
(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; In water; acetonitrile; tert-butyl alcohol; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)78234-7

Reference yield:

: 123444-68-8
(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

: 158587-54-3
(4S,5R,6R)-4-Azido-9-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-nonanoic acid

Guidance literature:: Multi-step reaction with 14 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

14: NaClO₂, NaH₂PO₄*H₂O / acetonitrile; 2-methyl-propan-2-ol; H₂O; various solvent(s) / 0.5 h / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; sodium chlorite; 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