(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

Base Information

Chemical Name:(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene
CAS No.:1420298-22-1
Molecular Formula:C₃₁H₄₆O₅Si
Molecular Weight:526.789
Hs Code.:

Synonyms:(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

Suppliers and Price of (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

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Technology Process of (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

There total 3 articles about (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-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: 86.0%

: 1420298-21-0
(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)hex-2-en-1-ol

: 3282-30-2
pivaloyl chloride

: 1420298-22-1
(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃; for 4h;
DOI:10.5012/bkcs.2012.33.11.3554

Reference yield:

: 131379-07-2
(2R,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

: 1420298-22-1
(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1: benzene / 0.08 h / Reflux

2: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -78 °C

3: dmap / dichloromethane / 4 h / 0 - 20 °C

With dmap; diisobutylaluminium hydride; In dichloromethane; toluene; benzene;
DOI:10.5012/bkcs.2012.33.11.3554

Reference yield:

: 158535-84-3
(2S,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

: 1420298-22-1
(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

2: benzene / 0.08 h / Reflux

3: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -78 °C

4: dmap / dichloromethane / 4 h / 0 - 20 °C

With dmap; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; toluene; benzene; 1: |Swern Oxidation;
DOI:10.5012/bkcs.2012.33.11.3554