ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Base Information

• Chemical Name: ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS No.: 1446347-61-0
• Molecular Formula: C₂₆H₃₆O₅Si
• Molecular Weight: 456.654

Synonyms:ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Chemical Property of ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Chemical Property:

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Technology Process of ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

There total 2 articles about ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 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: 92.0%

2,2-dimethoxy-propane (77-76-9) + ethyl (2S,3R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-2,3-dihydroxypentanoate → ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1446347-61-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c3ob40252e

Reference yield:

C23H30O3Si → ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1446347-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 24 h / 0 °C / Inert atmosphere

2: toluene-4-sulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

With methanesulfonamide; AD-mix β; toluene-4-sulfonic acid; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1039/c3ob40252e

Reference yield: 88.0%

ethyl (4S,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1446347-61-0) → [(4R,5R)-5-(2-[1-(tert-Butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (1446347-62-1)

Guidance literature:

With lithium borohydride; water; In diethyl ether; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c3ob40252e

upstream raw materials:

2,2-dimethoxy-propane

Downstream raw materials:

(+)-(2R,3R,4S,7S)-3-(((3R,4R)-3,4-dihydroxypentanoyl)oxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoic acid

(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

[(4R,5R)-5-(2-[1-(tert-Butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

[(4R,5R)-5-(2-[1-(tert-butyl)-1,1-diphenylsilyl]oxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methyl-1-benzenesulfonate

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