(2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane

Base Information

• Chemical Name: (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane
• CAS No.: 201933-46-2
• Molecular Formula: C₂₀H₂₅N₃O₂Si
• Molecular Weight: 367.523
• Mol file: 201933-46-2.mol

Synonyms:(2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane

Chemical Property of (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane

There total 6 articles about (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-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: 87.0%

(2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)butane-1,2-diol (374556-93-1) → (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane (201933-46-2)

Guidance literature:

(2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)butane-1,2-diol; With Trimethyl orthoacetate; pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;

With Acetyl bromide; triethylamine; at 0 - 20 ℃;

With potassium carbonate; In methanol; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2007.09.098

Reference yield: 87.0%

C20H27N3O3Si → (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane (201933-46-2)

Guidance literature:

With Acetyl bromide; potassium carbonate; Triethyl orthoacetate; In methanol;

DOI:10.1055/s-0035-1561987

Reference yield:

(S)-4-{(1S)-2-[(1,1-dimethylethyl)diphenylsilyloxy]-1-(hydroxy)ethyl}-2,2-dimethyl-1,3-dioxolane (183888-74-6) → (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane (201933-46-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2: 81 percent / tetramethylguanidinium azide / CH₂Cl₂ / -78 - 20 °C

3: 65 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 2 h / 0 °C

4: 79 percent / triphenylphosphane; diisopropyl azodicarboxylate / toluene / 2.5 h / 130 °C / 0.01 Torr

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; triphenylphosphine; tetramethylguanidinum azide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 4: Mitsunobu reaction;

DOI:10.1002/1099-0690(200108)2001:16<3089::AID-EJOC3089>3.0.CO;2-L

upstream raw materials:

(2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)butane-1,2-diol

(S)-4-{(1S)-2-[(1,1-dimethylethyl)diphenylsilyloxy]-1-(hydroxy)ethyl}-2,2-dimethyl-1,3-dioxolane

(2R,3R)-3-azido-4-tert-butyldiphenylsilyloxy-1,2-O-isopropylidenebutane-1,2-diol

Downstream raw materials:

methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-D-glycero-D-allo-heptafuranosiduronic acid

methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

(2R,3R)-3-amino-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane

methyl (5R)-5-C-[(2'R,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside