(+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

Base Information

Chemical Name:(+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene
CAS No.:279674-86-1
Molecular Formula:C₂₆H₄₇FO₃Si₂
Molecular Weight:482.827
Hs Code.:

Synonyms:(+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

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Technology Process of (+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

There total 5 articles about (+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene 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: 74.0%

: 100-39-0
benzyl bromide

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

: 279674-86-1
(+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

Guidance literature:: (+)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-en-1-ol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃;
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

: 279674-86-1
(+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

Guidance literature:: Multi-step reaction with 2 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

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; diethyl ether;
DOI:10.1016/S0957-4166(00)00482-1

Reference yield:

: 147410-74-0
(E)/(Z)-ethyl 3-[(S)-2,2-dimethyl-(1,3)-dioxolan-4-yl]-2-fluoroacrylate

: 279674-86-1
(+)-(4R)-6-benzyloxy-1-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxymethyl-4-fluorohex-2-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / conc. HCl / ethanol

2.1: DIBAL-H

2.2: NaBH₄; CeCl₃

3.1: 70 percent / propionic acid / 130 °C

4.1: 95 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -40 - -35 °C

5.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 74 percent / TBAI / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; sodium hydride; diisobutylaluminium hydride; propionic acid; In tetrahydrofuran; ethanol; 1.1: Hydrolysis / 1.2: Silylation / 2.1: Ring cleavage / 2.2: Reduction / 2.3: Silylation / 3.1: Condensation / 4.1: Reduction / 5.1: Metallation / 5.2: Benzylation;
DOI:10.1021/ol005665k