(4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene

Base Information

• Chemical Name: (4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene
• CAS No.: 855282-22-3
• Molecular Formula: C₂₆H₃₈O₄Si
• Molecular Weight: 442.671
• Mol file: 855282-22-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-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: 98.0%

tert-Butyl-((2R,3R,4S)-4-methoxy-2,3-bis-methoxymethoxy-5,5-dimethyl-hept-6-enyloxy)-diphenyl-silane (855282-51-8) → (4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene (855282-22-3)

Guidance literature:

With n-butanethiol; zinc dibromide; In dichloromethane; at 20 ℃; for 0.133333h;

DOI:10.1021/ja050728l

Reference yield:

(4S,5R,6R)-5,6-bis(methoxymethoxy)-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-hydroxy-1-heptene (855282-04-1) → (4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene (855282-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

2: 80 percent / pyridinium p-toluenesulfonate / propan-2-ol / 48 h / Heating

With pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1021/jo0615145

Reference yield:

(2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butyraldehyde (937166-57-9) → (4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene (855282-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / ZnBr₂ / CH₂Cl₂ / -78 - 0 °C

2: 98 percent / NaH / tetrahydrofuran

3: 98 percent / n-BuSH; ZnBr₂ / CH₂Cl₂ / 0.13 h / 20 °C

With n-butanethiol; sodium hydride; zinc dibromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja050728l

upstream raw materials:

tert-Butyl-((2R,3R,4S)-4-methoxy-2,3-bis-methoxymethoxy-5,5-dimethyl-hept-6-enyloxy)-diphenyl-silane

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

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

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

Downstream raw materials:

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

(4S,5S,6R)-6-benzyloxy-5,7-dihydroxy-3,3-dimethyl-4-methoxy-1-heptene

(4S,5S,6R)-6-benzyloxy-3,3-dimethyl-5,7-O-isopropylidene-4-methoxy-1-heptene

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