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

Base Information

• Chemical Name: (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane
• CAS No.: 1073828-70-2
• Molecular Formula: C₃₀H₄₃BrO₄Si
• Molecular Weight: 575.659
• Mol file: 1073828-70-2.mol

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

Chemical Property of (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane

There total 14 articles about (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-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: 85.0%

(2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran (1073828-69-9) → (2S,5S)-5-[(1R,2S,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane (1073828-88-2) + (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane (1073828-70-2)

Guidance literature:

With methanesulfonamide; AD-mix-β; In water; tert-butyl alcohol; at 20 ℃; for 20h; optical yield given as %de; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol801923y

Reference yield: 85.0%

(2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran (1073828-69-9) → (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane (1073828-70-2) + C30H43BrO4Si

Guidance literature:

With methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.joc.7b01973

Reference yield:

tert-butyl(pent-4-en-1-yloxy)diphenylsilane (132047-92-8) → (2S,5S)-5-[(1S,2R,3R)-5-bromo-1,2-dihydroxy-3-methyl-5-hexenyl]-2-(3-tert-butyldiphenylsilyloxypropyl)oxolane (1073828-70-2)

Guidance literature:

Multi-step reaction with 6 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 / 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

With titanium(IV) isopropylate; oxalyl dichloride; methanesulfonamide; C₄₆H₄₆N₂O₂; C₃₂H₄₄N₂O₂; dihydrogen peroxide; potassium hexamethylsilazane; 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; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;

DOI:10.1021/acs.joc.7b01973

upstream raw materials:

(2S,5S)-2-[(2E,3R)-5-bromo-3-methyl-1,5-hexadienyl]-5-[(3-tert-butyldiphenylsilyloxy)propyl]tetrahydrofuran

tert-butyl(pent-4-en-1-yloxy)diphenylsilane

(2S)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxypentane

(R)-1-(tert-butyldiphenylsilyloxy)-7-octen-4-ol

Downstream raw materials:

(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

(1R,2R,3R)-5-bromo-1-((2S,5S)-5-(3-(tert-butyldiphenylsilyloxy)propyl)oxolan-2-yl)-2-O-(4-methoxybenzyloxy)-3-methyl-5-hexen-1-ol