(3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol

Base Information

• Chemical Name: (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol
• CAS No.: 885322-70-3
• Molecular Formula: C₃₀H₄₈O₃Si₂
• Molecular Weight: 512.88
• Mol file: 885322-70-3.mol

Synonyms:(3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol

Chemical Property of (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol

There total 8 articles about (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-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:

(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal (885322-69-0) + allylmagnesium bromide (1730-25-2) → (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol (885322-70-3) + (3S,5S)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxyy]oct-7-ene-5-ol

Guidance literature:

allylmagnesium bromide; With (+)-B-methoxydiisocamphenylborane; In diethyl ether; at 0 - 20 ℃;

(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal; In diethyl ether; at -100 ℃; for 4h;

With sodium hydroxide; dihydrogen peroxide; In diethyl ether; water; at 20 ℃;

DOI:10.1021/jo060028e

Reference yield:

(3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene (885322-68-9) → (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol (885322-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 10 h / 20 °C

1.2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

2.2: diethyl ether / 4 h / -100 °C

2.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; water; 2.2: Brown asymmetric alkylation;

DOI:10.1021/jo060028e

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol (885322-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

1.2: diethyl ether / 4 h / -100 °C

1.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

2.1: 96 percent / imidazole / dimethylformamide / 20 °C

3.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 10 h / 20 °C

3.2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

4.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

4.2: diethyl ether / 4 h / -100 °C

4.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

With 1H-imidazole; osmium(VIII) oxide; 4-methylmorpholine N-oxide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; 1.2: Brown asymmetric alkylation / 4.2: Brown asymmetric alkylation;

DOI:10.1021/jo060028e

upstream raw materials:

(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

allylmagnesium bromide

(3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

(3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-yl acrylate

(1R)-1-{(2R)-4-oxo-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-2-pyranylmethyl}-3-butenyl acrylate

(3R,5R)-3-[(tert-butyldimethylsilyl)oxy]oct-7-enal-5-yl acrylate

(1R)-1-{(2S)-2-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-4-hydroxybutyl}-3-butenyl acrylate