(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

Base Information

Chemical Name:(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene
CAS No.:221627-53-8
Molecular Formula:C₃₁H₅₈O₃Si₂
Molecular Weight:534.971
Hs Code.:

Synonyms:(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

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Chemical Property of (3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

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Technology Process of (3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

There total 9 articles about (3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene 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: 82.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 221627-49-2
(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-3-methyloct-1-en-4-ol

: 221627-53-8
(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 6h;
DOI:10.1021/jo0503862

Reference yield:

: 106064-33-9
isobutyl 5-(benzyloxy)-3-oxopentanoate

: 221627-53-8
(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / H₂ / Ru₂Cl₄[(S)-BIMAP]Et₃N / methanol / 60 h / 2585.74 Torr

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

3.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C

4.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -50 °C

4.2: (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 26 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 4 h / -78 °C

5.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4.3: Brown asymmetric crotylation;
DOI:10.1021/jo0503862

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 221627-53-8
(3S,4S,6S)-8-benzyloxy-6-(tert-butyldimethylsilyl)oxy-4-(triisopropylsilyl)oxy-3-methyloct-1-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0.75 h / 0 °C

1.2: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -25 °C

1.3: 56 percent / tetrahydrofuran; hexane / 1 h / -25 °C

2.1: 99 percent / H₂ / Ru₂Cl₄[(S)-BIMAP]Et₃N / methanol / 60 h / 2585.74 Torr

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

4.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C

5.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -50 °C

5.2: (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 1 h / -78 °C

5.3: 26 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 4 h / -78 °C

6.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; hydrogen; sodium hydride; diisobutylaluminium hydride; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.3: Brown asymmetric crotylation;
DOI:10.1021/jo0503862