(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

Base Information

Chemical Name:(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone
CAS No.:152996-72-0
Molecular Formula:C₂₁H₃₅NO₃Si
Molecular Weight:377.599
Hs Code.:

Synonyms:(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

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Chemical Property of (3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

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Technology Process of (3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

There total 5 articles about (3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone 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: 91.0%

: 152996-71-9
(2S,3R) O-benzyl 2-(hydroxymethyl)-3-<(tri-i-propylsilyl)oxy>butanohydroxamate

: 152996-72-0
(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4020(01)87214-8

Reference yield:

: 152996-67-3
(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol

: 152996-72-0
(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 69.8 percent / 4 Angstroem molecular sieves, 1 M p-toluenesulfonic acid monohydrate / propan-2-ol

3: Jones reagent / acetone / 0.33 h

4: 1.) N-hydroxybenzotriazole hydrate, DCC; 2.) triethylamine / 1.) CH₃CN, 1 h, r.t; 2.) overnight, r.t.

5: DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / Ambient temperature; pH = 7

6: 91 percent / Ph₃P, DEAD / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; jones reagent; 4 A molecular sieve; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; isopropyl alcohol; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)87214-8

Reference yield:

: (2S,3R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyric acid

: 152996-72-0
(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) N-hydroxybenzotriazole hydrate, DCC; 2.) triethylamine / 1.) CH₃CN, 1 h, r.t; 2.) overnight, r.t.

2: DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / Ambient temperature; pH = 7

3: 91 percent / Ph₃P, DEAD / tetrahydrofuran / Ambient temperature

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)87214-8