(2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

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Chemical Name:(2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane
CAS No.:1073828-73-5
Molecular Formula:C₃₈H₄₉BrO₅Si
Molecular Weight:693.794
Hs Code.:

Synonyms:(2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

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Chemical Property of (2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

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Technology Process of (2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

There total 14 articles about (2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane 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: 88.0%

: 1073828-70-2
(2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 1073828-73-5
(2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/acs.joc.7b01973

Reference yield:

: 106731-75-3
(2S)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxypentane

: 1073828-73-5
(2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(l) chloride / tetrahydrofuran; diethyl ether / -50 °C / Inert atmosphere

1.2: 0.5 h / -50 °C / Inert atmosphere

2.1: dihydrogen peroxide; titanium(IV) isopropylate; C₃₂H₄₄N₂O₂ / dichloromethane; water / 72 h / 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.5 h / -65 °C / Inert atmosphere

4.2: 18 h / 20 °C / Inert atmosphere

5.1: methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol / 20 h / 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; oxalyl dichloride; methanesulfonamide; C₃₂H₄₄N₂O₂; dihydrogen peroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; copper(l) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1021/acs.joc.7b01973

Reference yield:

: 132047-92-8
tert-butyl(pent-4-en-1-yloxy)diphenylsilane

: 1073828-73-5
(2S,5S)-5-((1R,2R,3R)-5-bromo-1,2-dihydroxy-1,2-O-((RS)-4-methoxyphenylmethylene)-3-methyl-5-hexenyl)-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

Guidance literature:: Multi-step reaction with 7 steps

1.1: dihydrogen peroxide; titanium(IV) isopropylate; C₄₆H₄₆N₂O₂ / water / 24 h / 20 °C / Inert atmosphere

1.2: 48 h / 20 °C / Inert atmosphere

2.1: copper(l) chloride / tetrahydrofuran; diethyl ether / -50 °C / Inert atmosphere

2.2: 0.5 h / -50 °C / Inert atmosphere

3.1: dihydrogen peroxide; titanium(IV) isopropylate; C₃₂H₄₄N₂O₂ / dichloromethane; water / 72 h / 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

4.2: 2 h / 20 °C / Inert atmosphere

5.1: potassium hexamethylsilazane / toluene; N,N-dimethyl-formamide / 0.5 h / -65 °C / Inert atmosphere

5.2: 18 h / 20 °C / Inert atmosphere

6.1: methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol / 20 h / 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; oxalyl dichloride; methanesulfonamide; C₄₆H₄₆N₂O₂; C₃₂H₄₄N₂O₂; dihydrogen peroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; copper(l) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1021/acs.joc.7b01973