(2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran

Base Information

• Chemical Name: (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran
• CAS No.: 857634-85-6
• Molecular Formula: C₂₅H₄₄O₂S₂Si₂
• Molecular Weight: 496.926
• Mol file: 857634-85-6.mol

Synonyms:(2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran

Chemical Property of (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran

There total 3 articles about (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran 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: 45.0%

(S)-{[1-(tert-butyldimethylsilanyloxymethyl)-(E)-but-2-enyl]dimethylsilanyl}benzene (857634-84-5) + [1,3]dithian-2-yl-acetaldehyde (57688-55-8) → (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran (857634-85-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - -45 ℃; for 1.5h;

DOI:10.1021/ol0506821

Reference yield:

(E)-(S)-2-(Dimethyl-phenyl-silanyl)-pent-3-en-1-ol → (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran (857634-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / imidazole / dimethylformamide / 1 h

2: 45 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -78 - -45 °C

With 1H-imidazole; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0506821

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R,4S,5R)-2-(tert-butyldimethylsilanyloxymethyl)-3-(dimethylphenylsilanyl)-5-[1,3]dithian-2-ylmethyl-4-methyltetrahydrofuran (857634-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / imidazole / dimethylformamide / 1 h

2: 45 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -78 - -45 °C

With 1H-imidazole; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0506821

upstream raw materials:

(S)-{[1-(tert-butyldimethylsilanyloxymethyl)-(E)-but-2-enyl]dimethylsilanyl}benzene

[1,3]dithian-2-yl-acetaldehyde

tert-butyldimethylsilyl chloride