(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol

Base Information

Chemical Name:(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol
CAS No.:498554-21-5
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

Synonyms:(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol

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

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

There total 9 articles about (1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol 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: 89.0%

: 69739-34-0
t-butyldimethylsiyl triflate

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

: (1S,3R,6R,8S,9S,10S)-8-allyl-9-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-10-ol

: 498554-21-5
(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)01329-7

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

: 498554-21-5
(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °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

Reference yield:

: 498554-12-4
4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

: 498554-21-5
(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C

2.2: 85 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 11 h / 23 °C

3.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

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

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

4.3: 93 percent / tetrahydrofuran / -78 - 0 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C

6.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; titanocene dichloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; toluene; 1.2: Tebbe olefination;
DOI:10.1016/S0040-4020(02)01329-7