(2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane

Base Information

• Chemical Name: (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane
• CAS No.: 123833-71-6
• Molecular Formula: C₁₇H₂₈O₃Si
• Molecular Weight: 308.493
• Mol file: 123833-71-6.mol

Synonyms:(2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane

Chemical Property of (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane

There total 6 articles about (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane 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: 98.0%

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol (78469-85-9,78513-07-2,78513-15-2,84621-89-6,87172-27-8,95672-91-6,98048-62-5,98048-63-6,78513-12-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane (123833-71-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(01)01048-6

Reference yield:

(E)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-2-butene (151359-19-2) → ((2R,3R)-3-Benzyloxymethyl-oxiranylmethoxy)-tert-butyl-dimethyl-silane + (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane (123833-71-6)

Guidance literature:

With Oxone; ethylenediaminetetraacetic acid; chiral ketone C₂₆H₄₀O₇; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 12h; pH=7 - 7.5; Further Variations:; Reagents; Product distribution;

DOI:10.1021/jo050928f

Reference yield:

(E)-4-(benzyloxy)-2-buten-1-ol (80885-30-9,81028-03-7,69152-88-1) → (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane (123833-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Ti(OiPr)4; (+)-DET; t-BuOOH / 18 h / -18 °C

2: 98 percent / imidazole / dimethylformamide / 2 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In N,N-dimethyl-formamide; 1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)01048-6

upstream raw materials:

benzyl bromide

(2S,3S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,3-epoxy-1-butanol

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₁₇H₂₉N₃O₃Si

C₁₇H₂₉N₃O₃Si

(2S,3S)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol

(2S,3S)-3-(benzyloxy)methyl-2-(tert-butyldimethylsiloxy)methyl-1-<(4-methylphenyl)sulfonyl>aziridine