(2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

Base Information

Chemical Name:(2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol
CAS No.:1616247-09-6
Molecular Formula:C₂₈H₄₂O₆Si
Molecular Weight:502.723
Hs Code.:

Synonyms:(2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

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Chemical Property of (2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

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Technology Process of (2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

There total 2 articles about (2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-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:

: 877373-38-1
(2S,3R)-2,3-bis(methoxymethoxy)-4-[(1,1-dimethylethyl)diphenylsilyl]oxybutyraldehyde

: 5162-44-7
1-bromo-4-butene

: 1616247-09-6
(2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

: 1616247-10-9
(2R,3R,4R)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

Guidance literature:: 1-bromo-4-butene; With magnesium;

(2S,3R)-2,3-bis(methoxymethoxy)-4-[(1,1-dimethylethyl)diphenylsilyl]oxybutyraldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 5h; diastereoselective reaction;
DOI:10.1016/j.tetasy.2014.04.011

Reference yield:

: 877373-78-9
(2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butan-1-ol

: 1616247-09-6
(2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

: 1616247-10-9
(2R,3R,4R)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

1.2: 0.33 h / -78 - 20 °C / Inert atmosphere

2.1: magnesium

2.2: 5 h / 0 - 20 °C

With oxalyl dichloride; magnesium; dimethyl sulfoxide; In dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Grignard Reaction / 2.2: |Grignard Reaction;
DOI:10.1016/j.tetasy.2014.04.011

Reference yield: 85.0%

: 1616247-09-6
(2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol

: 1616247-11-0
(5S,6R,7R)-8-(tert-butyldiphenylsilyloxy)-6,7-bis(methoxymethoxy)octane-1,5-diol

Guidance literature:: (2R,3R,4S)-1-(tert-butyldiphenylsilyloxy)-2,3-bis(methoxymethoxy)oct-7-en-4-ol; With dimethylsulfide borane complex; In tetrahydrofuran; at -10 - 20 ℃; for 3h;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;
DOI:10.1016/j.tetasy.2014.04.011