(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

Base Information

Chemical Name:(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene
CAS No.:947373-35-5
Molecular Formula:C₃₂H₅₂O₈S₂Si₂
Molecular Weight:685.063
Hs Code.:

Synonyms:(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

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Chemical Property of (2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

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Technology Process of (2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

There total 3 articles about (2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-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: 92.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 74862-83-2
(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-dihydroxy-hex-3-ene

: 947373-35-5
(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 7h;
DOI:10.1021/jo070462w

Reference yield:

: 3427-24-5
(2S,3E,5S)-1,2,5,6-tetrahydroxy-1,2:5,6-di-O-isopropylidene-hex-3-ene

: 947373-35-5
(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / Amberlyst 15 / methanol / 24 h / 20 °C

2.1: Bu₂SnO / toluene / 20 h / Heating

2.2: 66 percent / toluene / 23 h / 20 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 7 h / 0 °C

With 2,6-dimethylpyridine; Amberlyst 15; di(n-butyl)tin oxide; In methanol; dichloromethane; toluene;
DOI:10.1021/jo070462w

Reference yield:

: 6027-47-0
(2S,3E,5S)-1,2,5,6-tetrahydroxy-hex-3-ene

: 947373-35-5
(2R,3E,5R)-1,6-di-(p-toluenesulfonyloxy)-2,5-bis-(tert-butyldimethylsilyloxy)-hex-3-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: Bu₂SnO / toluene / 20 h / Heating

1.2: 66 percent / toluene / 23 h / 20 °C

2.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 7 h / 0 °C

With 2,6-dimethylpyridine; di(n-butyl)tin oxide; In dichloromethane; toluene;
DOI:10.1021/jo070462w