(4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Base Information

Chemical Name:(4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
CAS No.:1388144-83-9
Molecular Formula:C₂₉H₄₂O₅Si
Molecular Weight:498.735
Hs Code.:

Synonyms:(4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

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Chemical Property of (4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

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Technology Process of (4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

There total 10 articles about (4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-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: 95.0%

: 1388144-82-8
(2S,3R,7R)-ethyl 2,3-dihydroxy-7-(tert-butyldiphenylsilanyloxy)octanoate

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

: 1388144-83-9
(4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tetasy.2012.05.017

Reference yield:

: 1388144-80-6
((R)-6-(4-methoxybenzyloxy)hexan-2-yloxy)(tert-butyl)diphenylsilane

: 1388144-83-9
(4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

2.2: -78 - 20 °C

3.1: sodium hydride / diethyl ether; mineral oil / 0.17 h / -5 °C

3.2: 4 h / -5 - 20 °C

4.1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol

5.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C

With oxalyl dichloride; methanesulfonamide; AD-mix-β; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; mineral oil; tert-butyl alcohol; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Horner-Wadsworth-Emmons olefination / 4.1: Sharpless dihydroxylation;
DOI:10.1016/j.tetasy.2012.05.017

Reference yield:

: 1388144-81-7
(R,E)-ethyl 7-tert-butyldiphenylsilanyloxyoct-2-enoate

: 1388144-83-9
(4S,5R)-ethyl-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol

2: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C

With methanesulfonamide; AD-mix-β; toluene-4-sulfonic acid; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless dihydroxylation;
DOI:10.1016/j.tetasy.2012.05.017