(2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

Base Information

Chemical Name:(2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol
CAS No.:768386-42-1
Molecular Formula:C₂₆H₃₈O₄Si
Molecular Weight:442.671
Hs Code.:

Synonyms:(2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

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Chemical Property of (2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

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Technology Process of (2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

There total 4 articles about (2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol 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:

: 1779-49-3
Methyltriphenylphosphonium bromide

: 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-D-xylose

: 768386-42-1
(2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 0 - 20 ℃; for 1h;

2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-D-xylose; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 20 ℃; for 4h;
DOI:10.1039/b406280a

Reference yield:

: 138535-84-9
2,3-di-O-benzyl-D-xylose diethyl dithioacetal

: 768386-42-1
(2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: aq. HgCl₂; HgO / acetone / 3 h / 60 °C

3.1: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 - 20 °C

3.2: 2.74 g / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 4 h / 20 °C

With 1H-imidazole; n-butyllithium; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; N,N-dimethyl-formamide; acetone; 3.2: Wittig methylenation;
DOI:10.1039/b406280a

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 768386-42-1
(2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: aq. HgCl₂; HgO / acetone / 3 h / 60 °C

3.1: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 - 20 °C

3.2: 2.74 g / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 4 h / 20 °C

With 1H-imidazole; n-butyllithium; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; N,N-dimethyl-formamide; acetone; 3.2: Wittig methylenation;
DOI:10.1039/b406280a