(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

Base Information

Chemical Name:(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran
CAS No.:863660-12-2
Molecular Formula:C₂₂H₃₃BO₄
Molecular Weight:372.313
Hs Code.:

Synonyms:(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

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Chemical Property of (2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

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Technology Process of (2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

There total 1 articles about (2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran 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:

: 863662-92-4
(-)-2-((2R,6S)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethanol

: 863660-12-2
(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; sulfur trioxide; pyridine / CH₂Cl₂; dimethylsulfoxide / 5 h / 20 °C

2: 89 percent / LiI; CrCl₂ / tetrahydrofuran / 16 h / 20 °C

With pyridine; chromium dichloride; sulfur trioxide; triethylamine; lithium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo0507993

Reference yield: 70.0%

: 863660-12-2
(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

: 164014-40-8
2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

: 863660-04-2
5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Guidance literature:: (2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran; 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one; With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 60 ℃; for 24h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran;
DOI:10.1021/jo0507993

Reference yield:

: 863660-12-2
(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

: 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran / 24 h / 60 °C

1.2: 70 percent / NaOH; H₂O₂ / tetrahydrofuran

2.1: 99 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C

3.1: 98 percent / triethylamine; sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 5 h / 0 - 20 °C

4.1: NaHMDS / diethyl ether / 0.25 h / -78 °C

4.2: 83 percent / diethyl ether / 15 h / 20 °C

With pyridine; potassium phosphate; sulfur trioxide; hydrogen; sodium hexamethyldisilazane; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 1.1: Suzuki reaction;
DOI:10.1021/jo0507993