(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

Base Information

Chemical Name:(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester
CAS No.:1264193-82-9
Molecular Formula:C₄₀H₅₇BrN₂O₇Si
Molecular Weight:785.891
Hs Code.:

(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

Synonyms:(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

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Chemical Property of (4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

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Technology Process of (4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

There total 8 articles about (4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester 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: 57.0%

: 1264193-96-5
C₄₀H₅₈N₂O₇Si

: 1264193-82-9
(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

Guidance literature:: C₄₀H₅₈N₂O₇Si; With lithium diisopropyl amide; In tetrahydrofuran; at -100 ℃; for 1h; Inert atmosphere;

With N-Bromosuccinimide; In tetrahydrofuran; at -100 - -78 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ol102860r

Reference yield:

: 1264193-78-3
C₁₄H₁₈O₅

: 1264193-82-9
(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: titanium tetrachloride / dichloromethane / 120 h / -78 - -20 °C / Inert atmosphere

2.1: water; N,N-dimethyl-formamide / 0.17 h / Microwave irradiation; Heating; Sealed tube

3.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 20 °C

4.1: phenyllithium / tetrahydrofuran; dibutyl ether / 0 - 20 °C / Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

5.1: pyridine / dichloromethane / 1 h / -5 °C / Inert atmosphere

6.1: lithium diisopropyl amide / tetrahydrofuran / -78 - 0 °C / Inert atmosphere

6.2: 18 h / -78 - -20 °C / Inert atmosphere

7.1: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

8.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -100 °C / Inert atmosphere

8.2: 4 h / -100 - -78 °C / Inert atmosphere

With pyridine; dmap; palladium 10% on activated carbon; hydrogen; titanium tetrachloride; phenyllithium; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dibutyl ether; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Maitland-Japp reaction;
DOI:10.1021/ol102860r

Reference yield:

: 1287312-82-6
C₂₅H₄₃NO₆Si

: 1264193-82-9
(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: phenyllithium / tetrahydrofuran; dibutyl ether / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 1 h / -5 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran / -78 - 0 °C / Inert atmosphere

3.2: 18 h / -78 - -20 °C / Inert atmosphere

4.1: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

5.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -100 °C / Inert atmosphere

5.2: 4 h / -100 - -78 °C / Inert atmosphere

With pyridine; dmap; phenyllithium; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; dibutyl ether; acetonitrile;
DOI:10.1021/ol102860r