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

Base Information

• Chemical Name: (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-yl acrylate
• CAS No.: 885322-71-4
• Molecular Formula: C₃₃H₅₀O₄Si₂
• Molecular Weight: 566.929
• Mol file: 885322-71-4.mol

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

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

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-yl acrylate

There total 8 articles about (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-yl acrylate 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: 94.0%

(3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-ol (885322-70-3) + acryloyl chloride (814-68-6,25189-84-8) → (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-yl acrylate (885322-71-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo060028e

Reference yield:

(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal (885322-69-0) → (3S,5R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]oct-7-ene-5-yl acrylate (885322-71-4)

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: 94 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With triethylamine; (+)-B-methoxydiisocamphenylborane; In diethyl ether; dichloromethane; 1.2: Brown asymmetric alkylation;

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-yl acrylate (885322-71-4)

Guidance literature:

Multi-step reaction with 3 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

3.1: 94 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

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

DOI:10.1021/jo060028e

upstream raw materials:

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

acryloyl chloride

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

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

Downstream raw materials:

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

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