(2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Base Information

• Chemical Name: (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal
• CAS No.: 145655-02-3
• Molecular Formula: C₂₈H₄₁NO₄Si
• Molecular Weight: 483.723
• Mol file: 145655-02-3.mol

Synonyms:

Chemical Property of (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

There total 11 articles about (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal 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%

(1'R,2'S)-2-<2'-<(N-tert-Butoxycarbonyl)benzylamino>-1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole (145655-10-3) → (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal (145655-02-3)

Guidance literature:

DOI:10.1016/S0040-4039(00)60888-2

Reference yield:

(1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole (145655-01-2) → (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal (145655-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, DMAP / dimethylformamide / 1 h / Ambient temperature

2: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / Ambient temperature

3: 1.) NaBH₄, 2.) aq. HgCl₂ / 1.) MeOH, r.t., 10 min, 2.) CH₃CN, r.t., 15 min

With dmap; sodium tetrahydroborate; 4 A molecular sieve; triethylamine; mercury dichloride; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00129a037

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal (145655-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, DMAP / dimethylformamide / 1 h / Ambient temperature

2: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / Ambient temperature

3: 1.) NaBH₄, 2.) aq. HgCl₂ / 1.) MeOH, r.t., 10 min, 2.) CH₃CN, r.t., 15 min

With dmap; sodium tetrahydroborate; 4 A molecular sieve; triethylamine; mercury dichloride; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00129a037

upstream raw materials:

(1'R,2'S)-2-<2'-<(N-tert-Butoxycarbonyl)benzylamino>-1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole

t-butyldimethylsiyl triflate

(1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole

di-tert-butyl dicarbonate

Downstream raw materials:

Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenyl-2(E)-hexenoate

(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one

(5S,1'S)-5-<1'--3'-methylbutyl>dihydrofuran-2(3H)-one

(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one