(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

Base Information

Chemical Name:(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol
CAS No.:498554-20-4
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

Synonyms:(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

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Chemical Property of (1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

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Technology Process of (1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

There total 12 articles about (1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol 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: 99.0%

: 498554-19-1
(1S,2R,4R,7R,9S,10S)-9-allyl-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadecane

: 498554-20-4
(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)01329-7

Reference yield: 92.0%

: 53263-19-7
3-(β-D-glucopyranosyl)prop-1-ene

: 1125-88-8
benzaldehyde dimethyl acetal

: 498554-20-4
(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

Guidance literature:: With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃; for 22h;
DOI:10.1016/j.bmcl.2005.12.048

Reference yield:

: 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucopyranose

: 498554-20-4
(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: titanocene dichloride / toluene / 72 h / 23 °C

2.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C

3.2: 85 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 11 h / 23 °C

4.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

5.1: BuLi / tetrahydrofuran / 1 h / -78 °C

5.2: CuCN / tetrahydrofuran / -78 - 0 °C

5.3: 93 percent / tetrahydrofuran / -78 - 0 °C

6.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; titanocene dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Swern oxidation / 2.2: Tebbe olefination;
DOI:10.1016/S0040-4020(02)01329-7