(1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

Base Information

Chemical Name:(1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane
CAS No.:843609-73-4
Molecular Formula:C₂₇H₃₀O₂Si
Molecular Weight:414.62
Hs Code.:

Synonyms:(1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

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Chemical Property of (1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

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Technology Process of (1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

There total 5 articles about (1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane 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: 25.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 625389-71-1
(+)-(1R,2S)-(2-hydroxymethyl-1-phenyl-cyclopropyl)-methanol

: 625389-74-4
(1S,2R)-1-(tert-butyldiphenylsilyloxy)methyl-2-formyl-2-phenylcyclopropane

: 843609-73-4
(1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

Guidance literature:: tert-butylchlorodiphenylsilane; (+)-(1R,2S)-(2-hydroxymethyl-1-phenyl-cyclopropyl)-methanol; With sodium hydride; In tetrahydrofuran; at -20 ℃; for 1h;

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; Further stages.;
DOI:10.1016/j.tet.2004.05.063

Reference yield:

: (Z)-4-(tert-butyldiphenylsiloxy)-3-phenylbut-2-en-1-yl acetate

: 843609-73-4
(1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

Guidance literature:: Multi-step reaction with 3 steps

1: sodium methylate; methanol / diethyl ether / 20 °C

2: (S)-2-(methanesulfonyl)amino-1-(p-toluenesulfonyl)amino-3-phenylpropane; diethylzinc / hexane; dichloromethane / 3 h / -40 - 0 °C / Inert atmosphere

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

With methanol; diethylzinc; sodium methylate; (S)-2-(methanesulfonyl)amino-1-(p-toluenesulfonyl)amino-3-phenylpropane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 2: |Simmons-Smith Cyclopropanation;
DOI:10.1016/j.tetasy.2016.12.010

Reference yield:

: (Z)-4-hydroxy-3-phenylbut-2-en-1-yl acetate

: 843609-73-4
(1R,2S)-1-tert-butyldiphenylsilyloxymethyl-2-formyl-1-phenylcyclopropane

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 24 h / 20 °C / Inert atmosphere

2: sodium methylate; methanol / diethyl ether / 20 °C

3: (S)-2-(methanesulfonyl)amino-1-(p-toluenesulfonyl)amino-3-phenylpropane; diethylzinc / hexane; dichloromethane / 3 h / -40 - 0 °C / Inert atmosphere

4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

With pyridine; methanol; diethylzinc; sodium methylate; (S)-2-(methanesulfonyl)amino-1-(p-toluenesulfonyl)amino-3-phenylpropane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 3: |Simmons-Smith Cyclopropanation;
DOI:10.1016/j.tetasy.2016.12.010