(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

Base Information

Chemical Name:(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane
CAS No.:240820-96-6
Molecular Formula:C₃₂H₄₂O₆Si
Molecular Weight:550.767
Hs Code.:

Synonyms:(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

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Chemical Property of (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

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Technology Process of (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

There total 3 articles about (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane 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: 93.0%

: 240820-95-5
(2R,4S,5R)-4-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-(3,4-dimethoxy-phenyl)-[1,3]dioxane-5-carbaldehyde

: 240820-96-6
(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

Guidance literature:: With sodium tetrahydroborate; In diethyl ether; at 20 ℃; for 1h;
DOI:10.1248/cpb.47.1288

Reference yield: 93.0%

: 240820-94-4
1-[(2R,4S,5S)-4-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-(3,4-dimethoxy-phenyl)-[1,3]dioxan-5-yl]-ethane-1,2-diol

: 240820-96-6
(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

Guidance literature:: With lithium borohydride; In diethyl ether; Ambient temperature;
DOI:10.1055/s-1999-2730

Reference yield:

: tert-Butyl-{(R)-2-[(2R,4S,5R)-2-(3,4-dimethoxy-phenyl)-5-vinyl-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane

: 240820-96-6
(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-1,3-[(R)-3,4-dimethoxybenzylidenedioxy]-4-methylpentane

Guidance literature:: Multi-step reaction with 3 steps

1: OsO₄; NMO / acetone; H₂O / 20 h / 20 °C

2: NaIO₄ / tetrahydrofuran / 1 h / 20 °C

3: 93 percent / NaBH₄ / diethyl ether / 1 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; diethyl ether; water; acetone; 1: dihydroxylation / 2: oxidative cleavage / 3: Reduction;
DOI:10.1248/cpb.47.1288