(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

Base Information

Chemical Name:(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene
CAS No.:855282-04-1
Molecular Formula:C₂₉H₄₄O₆Si
Molecular Weight:516.75
Hs Code.:

Synonyms:(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

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Chemical Property of (4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

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Technology Process of (4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

There total 5 articles about (4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene 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: 90.0%

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

: 104108-29-4
prenyl tributylstannane

: 855282-04-1
(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

Guidance literature:: With zinc dibromide; In dichloromethane; at -78 - 0 ℃; for 8h;
DOI:10.1021/jo0615145

Reference yield:

: 166734-76-5
(2R,3R)-2,3-bis(methoxymethoxy)butane-1,4-diol

: 855282-04-1
(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / n-BuLi / tetrahydrofuran / 4 h / 0 - 20 °C

2: 90 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / -78 - 20 °C

3: 90 percent / ZnBr₂ / CH₂Cl₂ / 8 h / -78 - 0 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;
DOI:10.1021/jo0615145

Reference yield:

: 159593-22-3
diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate

: 855282-04-1
(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / LiAlH₄ / diethyl ether / 2 h / Heating

2: 100 percent / n-BuLi / tetrahydrofuran / 4 h / 0 - 20 °C

3: 90 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / -78 - 20 °C

4: 90 percent / ZnBr₂ / CH₂Cl₂ / 8 h / -78 - 0 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Swern oxidation;
DOI:10.1021/jo0615145