(E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

Base Information

Chemical Name:(E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane
CAS No.:213816-71-8
Molecular Formula:C₃₆H₅₂O₆SSi
Molecular Weight:640.957
Hs Code.:

(E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

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Chemical Property of (E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

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Technology Process of (E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

There total 28 articles about (E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane 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:

: 162188-27-4
(2E)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-2-buten-1-ol

: 213816-71-8
(E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / N-bromosuccinimide; (C₆H₅)3P / CH₂Cl₂ / 2 h / 0 °C

2: (n-C₄H₉)Li / tetrahydrofuran; hexane / 0.67 h / -30 °C

With N-Bromosuccinimide; n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0040-4020(02)01474-6

Reference yield:

: 213816-86-5
(2R,3R,4S)-4-Acetyl-2-benzyloxymethyl-3-hydroxymethyl-2-methyl-cyclopentanone

: 213816-71-8
(E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / pyridine / 5 h / 20 °C

2: 90 percent / trimethylsilyl triflate / CH₂Cl₂ / 18 h / -40 °C

3: 98 percent / NaBH₄ / methanol / 0.25 h / 0 °C

4: 93 percent / N-phenylthiosuccinimide; (n-C₄H₉)3P; pyridine / 6 h / 20 °C

5: 100 percent / K₂CO₃ / methanol / 3 h / 20 °C

6: (n-C₄H₉)3P; pyridine / 5 h / 60 °C

7: 16.8 g / Oxone(R) / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

8: (n-C₄H₉)Li / tetrahydrofuran; hexane / 0.67 h / -30 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; oxone; N-(phenylthio)succinimide; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(02)01474-6

Reference yield:

: 213816-83-2
Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-4-hydroxy-6-hydroxymethyl-5-methyl-bicyclo[2.2.1]hept-2-yl ester

: 213816-71-8
(E)-{5-benzenesulfonyl-5-[(1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-3-cyclopentenyl]-3-methyl-2-pentenyloxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 13 steps

1: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: 100 percent / K₂CO₃ / methanol / 2 h / 20 °C

3: 90 percent / pyridinium chlorochromate; molecular sieves 4 Amgstroem / CH₂Cl₂ / 2 h / 20 °C

4: 86 percent / NaH; 15-crown-5 / toluene / 1 h / 20 °C

5: 97 percent / CH₃COOH / H₂O / 5 h / 20 °C

6: 100 percent / pyridine / 5 h / 20 °C

7: 90 percent / trimethylsilyl triflate / CH₂Cl₂ / 18 h / -40 °C

8: 98 percent / NaBH₄ / methanol / 0.25 h / 0 °C

9: 93 percent / N-phenylthiosuccinimide; (n-C₄H₉)3P; pyridine / 6 h / 20 °C

10: 100 percent / K₂CO₃ / methanol / 3 h / 20 °C

11: (n-C₄H₉)3P; pyridine / 5 h / 60 °C

12: 16.8 g / Oxone(R) / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

13: (n-C₄H₉)Li / tetrahydrofuran; hexane / 0.67 h / -30 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; oxone; N-(phenylthio)succinimide; 15-crown-5; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(02)01474-6