(4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 329010-34-6
• Molecular Formula: C₃₃H₄₆O₄Si₂
• Molecular Weight: 562.897
• Mol file: 329010-34-6.mol

Synonyms:

Chemical Property of (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane

There total 11 articles about (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane 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:

methyl (E)-6-(Benzyloxy)hex-3-enoate (274258-70-7) → (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane (329010-34-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

2: 95 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3: DIBAL-H / diethyl ether; cyclohexane / -78 °C

4: 5.98 g / benzene / 2 h / 50 °C

5: 82 percent / DIBAL-H / diethyl ether; cyclohexane / 0 °C

6: 80 percent / Ti(OPr-i)4; (R,R)-(+)-DET; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

7: 93 percent / CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

8: H₂ / Pd/C / ethyl acetate / 20 °C / 760.05 Torr

9: PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 - 20 °C

10: 480 mg / n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; camphor-10-sulfonic acid; hydrogen; sodium acetate; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; cyclohexane; water; ethyl acetate; tert-butyl alcohol; benzene; 4: Wittig olefination / 6: Katsuki-Sharpless asymmetric epoxidation / 10: Wittig olefination;

DOI:10.1021/jo0057194

Reference yield:

(E)-6-(benzyloxy)hex-3-enoic acid → (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane (329010-34-6)

Guidance literature:

Multi-step reaction with 11 steps

1: Me₃SiCl / 2 h / 20 °C

2: 90 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

3: 95 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

4: DIBAL-H / diethyl ether; cyclohexane / -78 °C

5: 5.98 g / benzene / 2 h / 50 °C

6: 82 percent / DIBAL-H / diethyl ether; cyclohexane / 0 °C

7: 80 percent / Ti(OPr-i)4; (R,R)-(+)-DET; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

8: 93 percent / CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

9: H₂ / Pd/C / ethyl acetate / 20 °C / 760.05 Torr

10: PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 - 20 °C

11: 480 mg / n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; chloro-trimethyl-silane; diethyl (2R,3R)-tartrate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; camphor-10-sulfonic acid; hydrogen; sodium acetate; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; cyclohexane; water; ethyl acetate; tert-butyl alcohol; benzene; 5: Wittig olefination / 7: Katsuki-Sharpless asymmetric epoxidation / 11: Wittig olefination;

DOI:10.1021/jo0057194

Reference yield:

(4R,5R)-5-(2-benzyloxyethyl)-4-(tert-butyldiphenylsilanyloxy)dihydrofuran-2-one (329010-26-6) → (4S)-4-[(2R,4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-(5-trimethylsilanylpent-2-(E)-en-4-ynyl)tetrahydrofuran-2-yl]-2,2-dimethyl-[1,3]dioxolane (329010-34-6)

Guidance literature:

Multi-step reaction with 8 steps

1: DIBAL-H / diethyl ether; cyclohexane / -78 °C

2: 5.98 g / benzene / 2 h / 50 °C

3: 82 percent / DIBAL-H / diethyl ether; cyclohexane / 0 °C

4: 80 percent / Ti(OPr-i)4; (R,R)-(+)-DET; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

5: 93 percent / CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

6: H₂ / Pd/C / ethyl acetate / 20 °C / 760.05 Torr

7: PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 - 20 °C

8: 480 mg / n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium acetate; diisobutylaluminium hydride; pyridinium chlorochromate; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; cyclohexane; ethyl acetate; benzene; 2: Wittig olefination / 4: Katsuki-Sharpless asymmetric epoxidation / 8: Wittig olefination;

DOI:10.1021/jo0057194

upstream raw materials:

methyl (E)-6-(Benzyloxy)hex-3-enoate

(4R,5R)-5-(2-benzyloxyethyl)-4-hydroxydihydrofuran-2-one

(4R,5R)-5-(2-benzyloxyethyl)-4-(tert-butyldiphenylsilanyloxy)dihydrofuran-2-one

(2E)(5R,6R)-8-benzyloxy-5-(tert-butyldiphenylsilanyloxy)-oct-2-ene-1,6-diol