(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

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Chemical Name:(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol
CAS No.:299917-21-8
Molecular Formula:C₃₆H₆₃BO₇
Molecular Weight:618.703
Hs Code.:

(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

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Chemical Property of (1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

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Technology Process of (1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

There total 9 articles about (1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol 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: 62.0%

: 300539-82-6
(3aR,4R,5R,6aS)-4-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

: triphenyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butyl]-phosphonium; bromide

: 299917-21-8
(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)00973-4

Reference yield:

: 58009-66-8
dimethyl (2-cyclohexyl-2-oxoethyl)phosphonate

: 299917-21-8
(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

Guidance literature:: Multi-step reaction with 7 steps

1: LiCl; Et₃N / tetrahydrofuran; CH₂Cl₂

2: NaBH₄; CeCl₃*7H₂O / methanol

3: K₂CO₃ / methanol

4: p-TsOH / CH₂Cl₂

5: H₂ / 10 percent Pd/C / ethyl acetate

6: DIBAL-H / toluene / -78 °C

7: 62 percent / (CH₃)3COK / tetrahydrofuran

With sodium tetrahydroborate; cerium(III) chloride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; 1: Condensation / 2: Reduction / 3: Hydrolysis / 4: Addition / 5: Hydrogenation / 6: Reduction / 7: Condensation;
DOI:10.1016/S0040-4039(00)00973-4

Reference yield:

: 120962-75-6
[3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-(tetrahydropyran-2-yloxy)-1-propenyl]-5-(tetrahydropyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

: 299917-21-8
(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / 10 percent Pd/C / ethyl acetate

2: DIBAL-H / toluene / -78 °C

3: 62 percent / (CH₃)3COK / tetrahydrofuran

With potassium tert-butylate; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene; 1: Hydrogenation / 2: Reduction / 3: Condensation;
DOI:10.1016/S0040-4039(00)00973-4