Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester
CAS No.:168777-42-2
Molecular Formula:C₃₁H₄₂O₄Si₂
Molecular Weight:534.843
Hs Code.:

Synonyms:Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

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Chemical Property of Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

There total 7 articles about Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl 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: 100.0%

: 108-24-7
acetic anhydride

: 168777-41-1
(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol

: 168777-42-2
Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

Guidance literature:: With pyridine; dmap; Ambient temperature;
DOI:10.1021/jo972066r

Reference yield:

: 159801-08-8
methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

: 168777-42-2
Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / AlMe₃ / CH₂Cl₂ / 40 °C

2: 53 percent / tetrahydrofuran / 20 - 50 °C

3: 89 percent / Me₄NH(OAc)3 / acetonitrile; acetic acid / -40 °C

4: 93 percent / PdCl₂, CuCl₂, AcONa / acetic acid / Ambient temperature

5: 100 percent / DIBAL-H / tetrahydrofuran / -78 °C

6: 85 percent / t-BuOK / diethyl ether / Ambient temperature

7: 100 percent / DMAP, pyridine / Ambient temperature

With pyridine; dmap; potassium tert-butylate; trimethylaluminum; sodium acetate; diisobutylaluminium hydride; copper dichloride; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/jo972066r

Reference yield:

: 168777-39-7
(3aR,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,2-b]furan-2-one

: 168777-42-2
Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / DIBAL-H / tetrahydrofuran / -78 °C

2: 85 percent / t-BuOK / diethyl ether / Ambient temperature

3: 100 percent / DMAP, pyridine / Ambient temperature

With pyridine; dmap; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether;
DOI:10.1021/jo972066r