(2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether)

Base Information

• Chemical Name: (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether)
• CAS No.: 441018-69-5
• Molecular Formula: C₂₉H₅₄O₄Si₂
• Molecular Weight: 522.916
• Mol file: 441018-69-5.mol

Synonyms:(2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether)

Chemical Property of (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether)

There total 7 articles about (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether) 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: 83.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol (441018-68-4) → (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether) (441018-69-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

(R)-benzyl glycidol (14618-80-5) → (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether) (441018-69-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / CuI / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 - 25 °C

2.2: 85 percent / NaH / tetrahydrofuran / 3 h / 25 °C

3.1: Et₃N / diethyl ether / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: 21.6 g / tetrahydrofuran; diethyl ether; hexane / 1.25 h / -78 - 0 °C

5.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

5.2: 58 percent / CH₂Cl₂ / 1.5 h / -78 °C

6.1: 76 percent / LiBH₄ / diethyl ether; methanol; tetrahydrofuran / 2 h / 0 °C

7.1: 83 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; copper(l) iodide; lithium borohydride; n-butyllithium; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

(2R)-1-(benzyloxy)-2-butanol (167354-12-3,128821-01-2) → (2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol bis(tert-butyldimethylsilyl ether) (441018-69-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 - 25 °C

1.2: 85 percent / NaH / tetrahydrofuran / 3 h / 25 °C

2.1: Et₃N / diethyl ether / -78 - 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: 21.6 g / tetrahydrofuran; diethyl ether; hexane / 1.25 h / -78 - 0 °C

4.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

4.2: 58 percent / CH₂Cl₂ / 1.5 h / -78 °C

5.1: 76 percent / LiBH₄ / diethyl ether; methanol; tetrahydrofuran / 2 h / 0 °C

6.1: 83 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; n-butyllithium; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(02)00040-6

upstream raw materials:

t-butyldimethylsiyl triflate

(2S,3S)-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-5-hexen-1,3-diol

(R)-benzyl glycidol

(2R)-1-(benzyloxy)-2-butanol

Refernces