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

Base Information

• Chemical Name: (3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene
• CAS No.: 885322-68-9
• Molecular Formula: C₂₈H₄₄O₂Si₂
• Molecular Weight: 468.827
• Mol file: 885322-68-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene 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: 97.0%

(3R)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol (127793-65-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene (885322-68-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/acs.jnatprod.8b00732

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene (885322-68-9)

Guidance literature:

Multi-step reaction with 2 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

With 1H-imidazole; (+)-B-methoxydiisocamphenylborane; In diethyl ether; N,N-dimethyl-formamide; 1.2: Brown asymmetric alkylation;

DOI:10.1021/jo060028e

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene (885322-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 - 20 °C

1.2: 2 h / 0 - 20 °C

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3.5 h / 80 °C

3.1: (R)-1,1'-Bi-2-naphthol; titanium(IV) isopropylate / toluene / 0.17 h / Molecular sieve

3.2: 35 h / -78 - -20 °C

4.1: 1H-imidazole / dichloromethane / 4 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 3.1: |Keck Asymmetric Allylation;

DOI:10.1021/acs.jnatprod.8b00732

upstream raw materials:

(3R)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol

tert-butylchlorodiphenylsilane

3-(tert-butyldimethylsilanyloxy)propionaldehyde

tert-butyldimethylsilyl chloride

Downstream raw materials:

Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

(1R,3R,8E)-1-allyl-3-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-5,7-dioxo-9-phenyl-8-nonenyl acrylate

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

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