(4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

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Chemical Name:(4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester
CAS No.:866423-20-3
Molecular Formula:C₃₁H₄₆O₅Si
Molecular Weight:526.789
Hs Code.:

Synonyms:(4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

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Chemical Property of (4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

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Technology Process of (4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

There total 7 articles about (4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl 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: 89.0%

: 866423-19-0
(2R,3S,9R)-9-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-decanoic acid ethyl ester

: 77-76-9
2,2-dimethoxy-propane

: 866423-20-3
(4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; for 2h;
DOI:10.1016/j.tetlet.2005.07.153

Reference yield:

: 866423-15-6
(R)-8-Benzyloxy-octan-2-ol

: 866423-20-3
(4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / imidazole; DMAP / dimethylformamide / 2 h / 0 °C

2: 91 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -65 °C

4: tetrahydrofuran / 6 h / Heating

5: 94 percent / K₂CO₃; K₃Fe(CN)6; MeSO₂NH₂ / (DHQ)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6: 89 percent / p-TSA / CH₂Cl₂ / 2 h

With 1H-imidazole; dmap; oxalyl dichloride; methanesulfonamide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Swern oxidation / 4: Wittig reaction / 5: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2005.07.153

Reference yield:

: (R)-7-(tert-butyldiphenylsilyloxy)octanal

: 866423-20-3
(4R,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: tetrahydrofuran / 6 h / Heating

2: 94 percent / K₂CO₃; K₃Fe(CN)6; MeSO₂NH₂ / (DHQ)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

3: 89 percent / p-TSA / CH₂Cl₂ / 2 h

With methanesulfonamide; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1: Wittig reaction / 2: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2005.07.153