(3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

Base Information

Chemical Name:(3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene
CAS No.:343981-98-6
Molecular Formula:C₂₈H₄₈Br₂O₄Si₂
Molecular Weight:664.666
Hs Code.:

Synonyms:(3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

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Chemical Property of (3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

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Technology Process of (3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

There total 11 articles about (3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene 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:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 343981-98-6
(3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

8.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

10.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

10.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; triphenylphosphine; acetonitrile; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; 4.1: Sharpless assymetric dihydroxylation / 9.1: Dess-Martin oxidation / 10.1: Corey and Fuchs reaction;
DOI:10.1021/ja010195q

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 343981-98-6
(3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

8.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

10.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

10.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; triphenylphosphine; acetonitrile; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; 4.1: Sharpless assymetric dihydroxylation / 9.1: Dess-Martin oxidation / 10.1: Corey and Fuchs reaction;
DOI:10.1021/ja010195q

Reference yield:

: 86771-48-4
(4R)-4-[(4-methoxybenzyl)oxymethyl]-γ-butyrolactone

: 343981-98-6
(3Z,5R,7R)-5-(tert-butyldimethylsilyl)oxy-1,1-dibromo-8-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1,3-octadiene

Guidance literature:: Multi-step reaction with 9 steps

1.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

2.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

3.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

4.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

6.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

7.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

9.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

9.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; triphenylphosphine; acetonitrile; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 3.1: Sharpless assymetric dihydroxylation / 8.1: Dess-Martin oxidation / 9.1: Corey and Fuchs reaction;
DOI:10.1021/ja010195q