(2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane

Base Information

• Chemical Name: (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane
• CAS No.: 177186-42-4
• Molecular Formula: C₂₃H₃₃NO₃Si
• Molecular Weight: 399.605
• Mol file: 177186-42-4.mol

Synonyms:(2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane

Chemical Property of (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane

There total 3 articles about (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane 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: 89.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2S,3R)-3-amino-1,2-isopropylidenedioxy-butan-4-ol (176967-01-4) → (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane (177186-42-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 24h;

DOI:10.1016/0957-4166(96)00087-0

Reference yield:

ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate (114184-94-0) → (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane (177186-42-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / trifluoromethanesulfonic anhydride, 2,6-lutidine, tetramethylguanidinium azide / CHCl₃ / 12 h / 20 °C

2: 100 percent / LiAlH₄ / tetrahydrofuran / 1.) 20 deg C, 30 min, 2.) reflux, 2.5 h

3: 89 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 24 h

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; trifluoromethanesulfonic acid anhydride; triethylamine; tetramethylguanidinum azide; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1016/0957-4166(96)00087-0

Reference yield:

ethyl (2S,3S)-2-azido-3,4-isopropylidenedioxy-butanoate (177186-41-3) → (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane (177186-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / 1.) 20 deg C, 30 min, 2.) reflux, 2.5 h

2: 89 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 24 h

With dmap; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0957-4166(96)00087-0

upstream raw materials:

tert-butylchlorodiphenylsilane

(2S,3R)-3-amino-1,2-isopropylidenedioxy-butan-4-ol

ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate

ethyl (2S,3S)-2-azido-3,4-isopropylidenedioxy-butanoate

Downstream raw materials:

benzyl (4R,5S)-5-({[bis(benzyloxy)phosphoryl]oxy}methyl)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

benzyl (4R,5S)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

benzyl (4R,5S)-5-[(benzoyloxy)methyl]-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(2S,3R)-3-{[(benzyloxy)carbonyl]amino}-4-[(tert-butyldiphenylsilyl)oxy]-2-hydroxybutyl benzoate