(+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

Base Information

Chemical Name:(+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate
CAS No.:279674-88-3
Molecular Formula:C₂₂H₃₅FO₄Si
Molecular Weight:410.601
Hs Code.:

Synonyms:(+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

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Chemical Property of (+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

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Technology Process of (+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

There total 5 articles about (+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate 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: 80.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 279674-87-2
(-)-(4S)-4-O-benzyloxy-2-tert-butyldimethylsilyloxymethyl-2-fluorohexanal

: 279674-88-3
(+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(-)-(4S)-4-O-benzyloxy-2-tert-butyldimethylsilyloxymethyl-2-fluorohexanal; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/S0957-4166(00)00482-1

Reference yield:

: 279674-85-0
(+)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-en-1-ol

: 279674-88-3
(+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 74 percent / tetrabutylammonium iodide / tetrahydrofuran / 20 °C

2.1: O₃ / methanol / 0.5 h / -78 - 20 °C

2.2: 58 percent / Me₂S / methanol / 2 h / 0 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 80 percent / tetrahydrofuran / 1 h / -78 °C

With sodium hexamethyldisilazane; sodium hydride; ozone; In tetrahydrofuran; methanol; 3.2: Horner-Emmons olefination;
DOI:10.1016/S0957-4166(00)00482-1

Reference yield:

: 279674-84-9
(-)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-enoic acid ethylester

: 279674-88-3
(+)-(4R)-ethyl (E)-6-O-benzyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluoro-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 270 mg / lithium aluminum hydride / diethyl ether / 1.5 h / -40 - -35 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 74 percent / tetrabutylammonium iodide / tetrahydrofuran / 20 °C

3.1: O₃ / methanol / 0.5 h / -78 - 20 °C

3.2: 58 percent / Me₂S / methanol / 2 h / 0 °C

4.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: 80 percent / tetrahydrofuran / 1 h / -78 °C

With lithium aluminium tetrahydride; sodium hexamethyldisilazane; sodium hydride; ozone; In tetrahydrofuran; methanol; diethyl ether; 4.2: Horner-Emmons olefination;
DOI:10.1016/S0957-4166(00)00482-1